103854-64-4|8-Methoxyquinoline-2-carbaldehyde| Ambeed

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Quality Control of [ 103854-64-4 ] Purity: 95% SDS Specification

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Product Details of [ 103854-64-4 ]

CAS No. :	103854-64-4
Formula :	C₁₁H₉NO₂
M.W :	187.20
SMILES Code :	O=CC1=NC2=C(OC)C=CC=C2C=C1
MDL No. :	MFCD05864557
InChI Key :	WXFAZCYUMXZXBA-UHFFFAOYSA-N
Pubchem ID :	1548870

Safety of [ 103854-64-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H319
Precautionary Statements:	P305+P351+P338

Application In Synthesis of [ 103854-64-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 103854-64-4 ]

[ 103854-64-4 ] Synthesis Path-Downstream 1~35

1
[ 3033-80-5 ]
[ 103854-64-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With selenium(IV) oxide; In 1,4-dioxane; for 3h;Reflux;	The 2-methyl-8-methoxy quinoline (10) (3.50g, 20 . 2mmol) by adding 50 ml of dioxane, stirring to dissolve, then adding selenium dioxide (2.20g, 19 . 9mmol), heating reflow 3h. Cooling, filtering, adding activated carbon to the filtrate (1.0g), micro boils 15 min. Is filtered, concentrated under reduced pressure, to obtain yellow solid 3.52g, yield 93%.
93%	With selenium(IV) oxide; In 1,4-dioxane; for 4h;Reflux;	2-Methyl-8-methoxyquinoline (2) (3.50 g, 20.2 mmol) was addedDissolved in 80 mL of dioxane, followed by addition of selenium dioxide (2.20 g, 19.9 mmol) and heating under reflux for 4 h. Cooling, filtering, to the filtrate by adding activated carbon (4.0g), micro-boiling 10min. Filtered hot and concentrated under reduced pressure to give 3.52 g of a yellow solid in 93% yield, m.p. 103-104 C (103C).
81%	With selenium(IV) oxide; In 1,4-dioxane; at 110℃; for 2h;	8-Methoxy-2-methylquinoline (24) (28.9 mmol) was reacted withSeO2 (52.0 mmol, 1.8 eq) in anhydrous 1,4-dioxane (500 mL) at 110 Cfor 2 h to give 8-methoxyquinoline-2-carboxaldehyde (25). After completionof the reaction; the inorganic compounds were filtered off andpoured into cold water and partitioned with chloroform. The chloroformlayer was concentrated and the crude product obtained was purifiedby column chromatography over silica gel (60-120) usingchloroform as eluent. 8-Methoxyquinoline-2-carbaldehyde (25): yellow solid, yield 81%,m.p. 102-104 C; 1H NMR (CDCl3, 400 MHz): δ 10.32 (s, 1H), 8.29 (d,1H, J=8.4 Hz), 8.08 (d, 1H, J=8.4 Hz), 7.63 (t, 1H, J=8.0 Hz), 7.48(d, 1H, J=8.2 Hz), 7.16 (d, 1H, J=7.8 Hz), 4.17 (s, 3H); 13C NMR(CDCl3, 100 MHz): δ 193.7, 156.1, 151.5, 139.9, 137.3, 131.4, 129.8,119.6, 118.0, 108.6, 56.4; ESI-MS found m/z 187.98 [M+H]+.

With selenium(IV) oxide; In 1,4-dioxane; at 60 - 120℃; for 2.5h;

General procedure: o-Anisidine (29) (81.2 mmol) dissolved in 6 M HCl (190The resultant mixture was stirred for 5 min at a temperatureof 100C. Further, crotonaldehyde (30) (162.4 mmol, 2.0equiv.) was added to the reaction mixture dropwise followedby heating at 120C for 3 h. The aqueous layer was extractedwith chloroform after cooling and neutralization by aqueousNaOH solution. The organic layer was dried and purified bycolumn chromatography (silica gel 60-120 , chloroform aseluent) to get 8-methoxy-2-methylquinoline (31)26,27. It wasoxidized using SeO2 in 1,4-dioxane using the above-mentionedprocedure to obtain 8-methoxyquinoline-2-carbaldehyde(32).

References: [1]Patent: CN105294685,2016,A .Location in patent: Paragraph 0059.
[2]Patent: CN105418605,2016,A .Location in patent: Paragraph 0008; 0027; 0028.
[3]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 1453 - 1457.
[4]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3376 - 3380.
[5]ACS Chemical Neuroscience,2020,vol. 11,p. 4254 - 4261.
[6]Bioorganic Chemistry,2018,vol. 80,p. 591 - 601.
[7]New Journal of Chemistry,2007,vol. 31,p. 927 - 935.
[8]Journal of the Chemical Society,1954,p. 3782,3784.
[9]Chemische Berichte,1957,vol. 90,p. 758,761.
[10]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.
[11]Tetrahedron Letters,2018,vol. 59,p. 1130 - 1135.
[12]RSC Advances,2016,vol. 6,p. 30405 - 30411.
[13]Journal of the Indian Chemical Society,2020,vol. 97,p. 1251 - 1258.

2
[ 103854-64-4 ]
[ 10308-82-4 ]
[ 117638-71-8 ]

References: [1]Pharmazie,1987,vol. 42,p. 816 - 820.

3
[ 103854-64-4 ]
[ 112599-79-8 ]
[ 117638-74-1 ]

References: [1]Pharmazie,1987,vol. 42,p. 816 - 820.

4
[ 103854-64-4 ]
[ 117622-49-8 ]
[ 117638-73-0 ]

References: [1]Pharmazie,1987,vol. 42,p. 816 - 820.

5
[ 103854-64-4 ]
[ 117622-48-7 ]
[ 117638-75-2 ]

References: [1]Pharmazie,1987,vol. 42,p. 816 - 820.

6
[ 103854-64-4 ]
[ 117622-50-1 ]
, [ No CAS ]
[ 117638-78-5 ]

References: [1]Pharmazie,1987,vol. 42,p. 816 - 820.

7
[ 103854-64-4 ]
[ 36080-67-8 ]
N,N'-bis(8-methoxyquinolin-2-ylmethyl)-4,13-diazadibenzo-18-crown-6 [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 1453 - 1457.

8
[ 201230-82-2 ]
2-bromo-8-methoxyquinoline [ No CAS ]
[ 103854-64-4 ]

References: [1]Journal of Chemical Research - Part S,2002,p. 218 - 220.

9
[ 103854-64-4 ]
[ 141-43-5 ]
[ 936096-07-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	In toluene; at 50℃; for 3h;Reflux;	toward attire a water segregator and drying pipe compound is added in the three-necked flask 11 (4.40g, 23 . 5mmol), toluene (80 ml), stirring to dissolve, heating to 50 C, by adding 2-ethanolamine. Heating to reflux 3h, raw material 11 after the reaction. The reaction end of the, cooling, decompression and concentrated to obtain 4.98g yellow viscous compound, yield 92%. The product does not require further purification, can be directly used for the next step reaction.
92%	In toluene; at 60℃; for 4h;	Compound 3 (4.40 g, 23.5 mmol) and toluene (150 mL) were charged into a three-necked flask equipped with a water separator and a drying tube,Heated to 60 C,2-Ethanolamine was added. 4 hours after heating reflux 3 of raw materials reaction is completed. The reaction was quenched, cooled and concentrated under reduced pressure to give 4.98 g of a yellow viscous compound in 92% yield.

References: [1]Patent: CN105294685,2016,A .Location in patent: Paragraph 0061.
[2]Patent: CN105418605,2016,A .Location in patent: Paragraph 0008; 0029; 0030.
[3]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1701 - 1705.

10
[ 103854-64-4 ]
[ 21141-35-5 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

11
[ 103854-64-4 ]
[ 40817-03-6 ]
1,4-bis[2'-(8''-methoxyquinolin-2''-yl)ethenyl]benzene [ No CAS ]

References: [1]Journal of the Chinese Chemical Society,2005,vol. 52,p. 811 - 818.

12
[ 103854-64-4 ]
[ 40817-03-6 ]
1,4-bis[2'-(8''-methoxyquinolin-2''-yl)ethenyl]benzene [ No CAS ]

References: [1]Journal of the Chinese Chemical Society,2005,vol. 52,p. 811 - 818.

13
[ 103854-64-4 ]
(2,5-dimethoxy-1,4-phenylene)bis(methylene)bis(triphenylphosphonium bromide) [ No CAS ]
2,5-bis[2'-(8''-methoxyquinolin-2''-yl)ethenyl]-1,4-dimethoxybenzene [ No CAS ]

References: [1]Journal of the Chinese Chemical Society,2005,vol. 52,p. 811 - 818.

14
[ 826-81-3 ]
[ 103854-64-4 ]

References: [1]New Journal of Chemistry,2007,vol. 31,p. 927 - 935.
[2]Patent: CN105294685,2016,A .
[3]Patent: CN105418605,2016,A .
[4]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3376 - 3380.
[5]RSC Advances,2016,vol. 6,p. 30405 - 30411.
[6]ACS Chemical Neuroscience,2020,vol. 11,p. 4254 - 4261.

15
[ 103854-64-4 ]
10-methoxy-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

16
[ 103854-64-4 ]
10-methoxy-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

17
[ 103854-64-4 ]
[ 852402-76-7 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

18
[ 103854-64-4 ]
((S)-8-Methoxy-1,2,3,4-tetrahydro-quinolin-2-ylmethyl)-((S)-1-phenyl-ethyl)-amine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

19
[ 103854-64-4 ]
((R)-8-Methoxy-1,2,3,4-tetrahydro-quinolin-2-ylmethyl)-((S)-1-phenyl-ethyl)-amine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

20
[ 103854-64-4 ]
[ 852402-86-9 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

21
[ 103854-64-4 ]
[ 852402-81-4 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

22
[ 103854-64-4 ]
[ 852403-02-2 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

23
[ 103854-64-4 ]
[ 852403-07-7 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

24
[ 103854-64-4 ]
4-(10-methoxy-1,2,4,4a,5,6-hexahydro-pyrazino[1,2-a]quinolin-3-yl)-butylamine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

25
[ 103854-64-4 ]
4-(10-methoxy-1,2,4,4a,5,6-hexahydro-pyrazino[1,2-a]quinolin-3-yl)-butylamine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

26
[ 103854-64-4 ]
[ 852402-92-7 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

27
[ 103854-64-4 ]
[ 852402-97-2 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

28
[ 103854-64-4 ]
((S)-8-Methoxy-1,2,3,4-tetrahydro-quinolin-2-ylmethyl)-((S)-1-phenyl-ethyl)-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

29
[ 103854-64-4 ]
((R)-8-Methoxy-1,2,3,4-tetrahydro-quinolin-2-ylmethyl)-((S)-1-phenyl-ethyl)-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

30
[ 103854-64-4 ]
2-Chloro-1-{(S)-8-methoxy-2-[((S)-1-phenyl-ethylamino)-methyl]-3,4-dihydro-2H-quinolin-1-yl}-ethanone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

31
[ 103854-64-4 ]
2-Chloro-1-{(R)-8-methoxy-2-[((S)-1-phenyl-ethylamino)-methyl]-3,4-dihydro-2H-quinolin-1-yl}-ethanone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

32
[ 103854-64-4 ]
[(R)-1-(2-Chloro-acetyl)-8-methoxy-1,2,3,4-tetrahydro-quinolin-2-ylmethyl]-((S)-1-phenyl-ethyl)-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

33
[ 103854-64-4 ]
[(S)-1-(2-Chloro-acetyl)-8-methoxy-1,2,3,4-tetrahydro-quinolin-2-ylmethyl]-((S)-1-phenyl-ethyl)-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

34
[ 103854-64-4 ]
2-[4-(10-methoxy-1,2,4,4a,5,6-hexahydro-pyrazino[1,2-a]quinolin-3-yl)-butyl]-isoindole-1,3-dione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

35
[ 103854-64-4 ]
2-[4-(10-methoxy-1,2,4,4a,5,6-hexahydro-pyrazino[1,2-a]quinolin-3-yl)-butyl]-isoindole-1,3-dione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3171 - 3181.

Historical Records

Technical Information

• Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nomenclature of Ethers • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Preparation of Ethers • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Ethers • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 103854-64-4 ]

Aldehydes

A559030 [30464-91-6]

7-Methoxy-1H-indole-2-carbaldehyde

Similarity: 0.96

A130916 [14510-06-6]

8-Hydroxyquinoline-2-carbaldehyde

Similarity: 0.92

A213514 [21778-81-4]

5-Methoxy-1H-indole-2-carbaldehyde

Similarity: 0.88

A721458 [100063-12-5]

6-Ethoxyquinoline-2-carbaldehyde

Similarity: 0.87

A463369 [30464-93-8]

6-Methoxy-1H-indole-2-carbaldehyde

Similarity: 0.87

Ethers

A559030 [30464-91-6]

7-Methoxy-1H-indole-2-carbaldehyde

Similarity: 0.96

A213514 [21778-81-4]

5-Methoxy-1H-indole-2-carbaldehyde

Similarity: 0.88

A147619 [3033-80-5]

8-Methoxy-2-methylquinoline

Similarity: 0.88

A721458 [100063-12-5]

6-Ethoxyquinoline-2-carbaldehyde

Similarity: 0.87

A463369 [30464-93-8]

6-Methoxy-1H-indole-2-carbaldehyde

Similarity: 0.87

Related Parent Nucleus of
[ 103854-64-4 ]

Quinolines

A130916 [14510-06-6]

8-Hydroxyquinoline-2-carbaldehyde

Similarity: 0.92

A147619 [3033-80-5]

8-Methoxy-2-methylquinoline

Similarity: 0.88

A721458 [100063-12-5]

6-Ethoxyquinoline-2-carbaldehyde

Similarity: 0.87

A500472 [36456-52-7]

2-Formylquinolin-8-yl acetate

Similarity: 0.86

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H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 103854-64-4

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