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Structure of 42365-68-4

Chemical Structure| 42365-68-4

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Product Details of [ 42365-68-4 ]

CAS No. :42365-68-4
Formula : C8H12ClNO2
M.W : 189.64
SMILES Code : OC1=CC(CN)=CC=C1OC.[H]Cl
MDL No. :MFCD05664377
InChI Key :IEVBKUSXLSVMOB-UHFFFAOYSA-N
Pubchem ID :16217646

Safety of [ 42365-68-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H317-H319
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 42365-68-4 ]

* 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 [ 42365-68-4 ]

[ 42365-68-4 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 222533-34-8 ]
  • [ 42365-68-4 ]
  • 2
  • [ 42365-68-4 ]
  • [ 186371-01-7 ]
  • 2,4-dihydroxybenzoic acid N-(3-hydroxy-4-methoxy)benzylamide [ No CAS ]
  • 5
  • [ 1033330-31-2 ]
  • [ 42365-68-4 ]
  • (4Z)-6-bromo-4-[(3-hydroxy-4-methoxybenzyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione [ No CAS ]
  • 6
  • [ 943751-06-2 ]
  • [ 42365-68-4 ]
  • (4Z)-6-chloro-4-[(3-hydroxy-4-methoxybenzyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione [ No CAS ]
  • 7
  • [ 943752-10-1 ]
  • [ 42365-68-4 ]
  • 4-[(3-hydroxy-4-methoxybenzylamino)methylene]-6-methoxy-4H-isoquinoline-1,3-dione [ No CAS ]
  • 8
  • [ 943752-08-7 ]
  • [ 42365-68-4 ]
  • (4Z)-6-iodo-4-[(3-hydroxy-4-methoxybenzyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione [ No CAS ]
  • 9
  • [ 943749-78-8 ]
  • [ 42365-68-4 ]
  • (4Z)-4-[(3-hydroxy-4-methoxybenzyl)amino]methylene}-6-(1H-pyrrol-1-yl)isoquinoline-1,3(2H,4H)-dione [ No CAS ]
  • 10
  • [ 943750-47-8 ]
  • [ 42365-68-4 ]
  • (4Z)-6-fluoro4-[(3-hydroxy-4-methoxybenzyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione [ No CAS ]
  • 11
  • [ 1141841-39-5 ]
  • [ 42365-68-4 ]
  • [ 943347-54-4 ]
  • 12
  • [ 943750-48-9 ]
  • [ 42365-68-4 ]
  • (4Z)-4-[(3-hydroxy-4-methoxybenzyl)amino]methylene}-6-thien-3-ylisoquinoline-1,3(2H,4H)-dione [ No CAS ]
  • 13
  • [ 1141841-40-8 ]
  • [ 42365-68-4 ]
  • (4Z)-6-(3-furyl)-4-[(3-hydroxy-4-methoxybenzyl)amino]methylene}-3-ylisoquinoline-1,3(2H,4H)-dione [ No CAS ]
  • 14
  • [ 42365-68-4 ]
  • [ 78363-88-9 ]
  • (4Z)-4-[(3-hydroxy-4-methoxybenzyl)amino]methylene}-4H-isoquinoline-1,3-dione [ No CAS ]
  • 15
  • 3-hydroxy-4-methoxybenzaldehyde oxime [ No CAS ]
  • [ 42365-68-4 ]
YieldReaction ConditionsOperation in experiment
96% With hydrogenchloride; hydrogen; In water; isopropyl alcohol; at 20℃; under 7600.51 Torr;Autoclave; General procedure: A solutionof oxime 1a-k (23 mmol) in isopropyl alcohol (100 mL) was loaded into the autoclave with the fl uoroplastic bush, concentratedHCl (10.5 mL) was added, and a block of the regeneratedcatalyst was fi xed. Hydrogenation was conducted for 3-5 h at20 C and a hydrogen pressure of 10 atm, which was maintainedat this level during the reaction. The reaction course was monitoredby TLC. After the initial oxime disappeared completely,the reaction solution was poured out of the autoclave, the catalystblock was washed with methanol (3×30 mL), and the combinedsolutions were fi ltered from mechanical impurities. The solventwas evaporated, and analytically pure aromatic benzylamines3a-k were obtained.When hydrogenation was conducted in methanol (100 mL),solvent removal was followed by drying residue using azeotropicdistillation with isopropyl alcohol (250 mL). For the hydrogenationof compound 1k, the reaction mixture was additionallypurifi ed by refl ux with active carbon for 1 h. The blockcatalyst was regenerated directly in the reactor at 400 C ina hydrogen fl ow and further used in the next hydrogenationprocedure.
With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In ethanol; water; under 760.051 Torr; First step, hydroxyamine hydrochloride (1.29 g) and NaOAc (1.67 g) were added to a solution of 4-methoxy-3-hydroxybenzaldehyde (1.55 g) in EtOH (80 ml). The reaction mixture was stirred at room temperature for 6 h. EtOH was removed under reduced pressure. H2O (40 ml) was added to the residue, and extracted with EtOAc (3 × 40 ml). The EtOAc of the combined organic layer was removed by rotary evaporation under reduced pressure to yield 4-methoxy-3-hydroxybenzaldehyde oxime (1.45 g) as a pale yellowish solid. Second step, a solution of 4-methoxy-3-hydroxybenzaldehyde oxime (1.45 g) and concentrated HCl (1 ml) in EtOH (40 ml) was subjected to hydrogenation at atmospheric pressure in the presence of 10% Pd/C (85 mg). The reaction solution was filtered and the filtrate was concentrated to yield 4-methoxy-3-hydroxybenzylamine hydrochloride (1.59 g) as a white solid. Third step, a mixture of 4-methoxy-3-hydroxybenzylamine (469 mg, the hydrochloride), 6-chloropurine riboside (143 mg) and N, N-diisopropylethylamine (2 ml) in PrOH (40 ml) was heated to 70C and reacted for 8 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (30 : 1) to yield N6-(4-methoxy-3-hydroxybenzyl)-adenosine(164 mg) as a white solid: positive ESIMS 404 [M + H]+; negative ESIMS m/z 402 [M - H]- and 438 [M + Cl]-; 1H NMR (400 MHz, DMSO-d6): the adenosine moiety δ 8.35 (1H, s, H-2), 8.32 (1H, brs, -NH), 8.19 (1H, brs, H-8), 5.87 (1H, d, J= 6.0 Hz, H-1), 5.41 (1H, d, J=6.4 Hz, -OH), 5.37 (1H, m, -OH), 5.18 (1H, d, J= 4.8Hz, -OH), 4.60 (1H, m, H-2'), 4.13 (1H, m, H-3'), 3.95 (1H, m, H-4'), 3.66 (1H, m, H-5'a), 3.54 (1H, m, H-5'b); the 4-methoxy-3-hydroxybenzyl moiety δ 8.82 (1H, s, -OH), 6.80 (1H, d, J = 8.4 Hz, H-5"), 6.76 (1H, brs, H-2"), 6.70 (1H, brd, J = 8.4Hz, H-6"), 4.60 (2H, m, H-7"), 3.71 (3H, s, -OCH3); 13C NMR (125 MHz, DMSO-d6): the adenosine moiety δ 154.4 (C-6), 152.3 (C-2), 148.4 (C-4), 139.8 (C-8), 119.8 (C-5), 87.9 (C-1), 85.9 (C-4'), 73.4 (C-2'), 70.6 (C-3'), 61.6 (C-5'); the 4-methoxy-3-hydroxybenzyl moiety δ 146.5 (C-4"), 146.3 (C-3"), 132.6 (C-1), 117.8 (C-6"), 114.6 (C-2"), 112.1 (C-5"), 55.7 (-OCH3), 42.4 (C-7")o
1.59 g With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In ethanol; under 760.051 Torr; Second step, a solution of 4-methoxy-3-hydroxybenzaldehyde oxime (1.45 g) and concentrated HCl (1 ml) in EtOH (40 ml) was subjected to hydrogenation at atmospheric pressure in the presence of 10% Pd/C (85 mg). The reaction solution was filtered and the filtrate was concentrated to yield 4-methoxy-3-hydroxybenzylamine hydrochloride (1.59 g) as a white solid.
1.59 g With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In ethanol; water; 1.45 g of 4-methoxy-3-hydroxybenzaldehyde oxime was precisely weighed and added with 10% Pd / C (700 mg) and concentrated hydrochloric acid (8 mL), dissolved in EtOH (40 ml), under atmospheric pressure Hydrogenation of the reaction solution, filtration of the reaction solution, except for Pd / C, evaporation of the filtrate, addition of ethyl acetate, mixing well, dissolve, filtered, white solid1.59 g of 4-methoxy-3-hydroxymethylamine hydrochloride are obtained.

  • 17
  • [ 42365-68-4 ]
  • [ 2004-06-0 ]
  • N<SUP>6</SUP>-(4-methoxy-3-hydroxybenzyl)adenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In propan-1-ol; at 70℃; for 8.0h; First step, hydroxyamine hydrochloride (1.29 g) and NaOAc (1.67 g) were added to a solution of 4-methoxy-3-hydroxybenzaldehyde (1.55 g) in EtOH (80 ml). The reaction mixture was stirred at room temperature for 6 h. EtOH was removed under reduced pressure. H2O (40 ml) was added to the residue, and extracted with EtOAc (3 × 40 ml). The EtOAc of the combined organic layer was removed by rotary evaporation under reduced pressure to yield 4-methoxy-3-hydroxybenzaldehyde oxime (1.45 g) as a pale yellowish solid. Second step, a solution of 4-methoxy-3-hydroxybenzaldehyde oxime (1.45 g) and concentrated HCl (1 ml) in EtOH (40 ml) was subjected to hydrogenation at atmospheric pressure in the presence of 10% Pd/C (85 mg). The reaction solution was filtered and the filtrate was concentrated to yield 4-methoxy-3-hydroxybenzylamine hydrochloride (1.59 g) as a white solid. Third step, a mixture of 4-methoxy-3-hydroxybenzylamine (469 mg, the hydrochloride), 6-chloropurine riboside (143 mg) and N, N-diisopropylethylamine (2 ml) in PrOH (40 ml) was heated to 70C and reacted for 8 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (30 : 1) to yield N6-(4-methoxy-3-hydroxybenzyl)-adenosine(164 mg) as a white solid: positive ESIMS 404 [M + H]+; negative ESIMS m/z 402 [M - H]- and 438 [M + Cl]-; 1H NMR (400 MHz, DMSO-d6): the adenosine moiety δ 8.35 (1H, s, H-2), 8.32 (1H, brs, -NH), 8.19 (1H, brs, H-8), 5.87 (1H, d, J= 6.0 Hz, H-1), 5.41 (1H, d, J=6.4 Hz, -OH), 5.37 (1H, m, -OH), 5.18 (1H, d, J= 4.8Hz, -OH), 4.60 (1H, m, H-2'), 4.13 (1H, m, H-3'), 3.95 (1H, m, H-4'), 3.66 (1H, m, H-5'a), 3.54 (1H, m, H-5'b); the 4-methoxy-3-hydroxybenzyl moiety δ 8.82 (1H, s, -OH), 6.80 (1H, d, J = 8.4 Hz, H-5"), 6.76 (1H, brs, H-2"), 6.70 (1H, brd, J = 8.4Hz, H-6"), 4.60 (2H, m, H-7"), 3.71 (3H, s, -OCH3); 13C NMR (125 MHz, DMSO-d6): the adenosine moiety δ 154.4 (C-6), 152.3 (C-2), 148.4 (C-4), 139.8 (C-8), 119.8 (C-5), 87.9 (C-1), 85.9 (C-4'), 73.4 (C-2'), 70.6 (C-3'), 61.6 (C-5'); the 4-methoxy-3-hydroxybenzyl moiety δ 146.5 (C-4"), 146.3 (C-3"), 132.6 (C-1), 117.8 (C-6"), 114.6 (C-2"), 112.1 (C-5"), 55.7 (-OCH3), 42.4 (C-7")o
164 mg With N-ethyl-N,N-diisopropylamine; In propan-1-ol; at 70℃; for 8.0h; Third step, a mixture of 4-methoxy-3-hydroxybenzylamine (469 mg, the hydrochloride), 6-chloropurine riboside (143 mg) and N,N-diisopropylethylamine (2 ml) in PrOH (40 ml) was heated to 70 C. and reacted for 8 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (30:1) to yield N6-(4-methoxy-3-hydroxybenzyl)-adenosine (164 mg) as a white solid: positive ESIMS 404 [M+H]+; negative ESIMS m/z 402 [M-H]- and 438 [M+Cl]-; 1H NMR (400 MHz, DMSO-d6): the adenosine moiety δ 8.35 (1H, s, H-2), 8.32 (1H, brs, -NH), 8.19 (1H, brs, H-8), 5.87 (1H, d, J=6.0 Hz, H-1'), 5.41 (1H, d, J=6.4 Hz, -OH), 5.37 (1H, m, -OH), 5.18 (1H, d, J=4.8 Hz, -OH), 4.60 (1H, m, H-2'), 4.13 (1H, m, H-3'), 3.95 (1H, m, H-4'), 3.66 (1H, m, H-5'a), 3.54 (1H, m, H-5'b); the 4-methoxy-3-hydroxybenzyl moiety δ 8.82 (1H, s, -OH), 6.80 (1H, d, J=8.4 Hz, H-5"), 6.76 (1H, brs, H-2"), 6.70 (1H, brd, J=8.4 Hz, H-6"), 4.60 (2H, m, H-7"), 3.71 (3H, s, -OCH3); 13C NMR (125 MHz, DMSO-d6): the adenosine moiety δ 154.4 (C-6), 152.3 (C-2), 148.4 (C-4), 139.8 (C-8), 119.8 (C-5), 87.9 (C-1'), 85.9 (C-4'), 73.4 (C-2'), 70.6 (C-3'), 61.6 (C-5'); the 4-methoxy-3-hydroxybenzyl moiety δ 146.5 (C-4"), 146.3 (C-3"), 132.6 (C-1"), 117.8 (C-6"), 114.6 (C-2"), 112.1 (C-5"), 55.7 (-OCH3), 42.4 (C-7").
164 mg With N-ethyl-N,N-diisopropylamine; In propan-1-ol; at 70℃; for 8.0h; 9 mg of 4-methoxy-3-hydroxymethylamine hydrochloride was taken and 6-chloropurine nucleoside (143 mg) and N,N-diisopropylethylamine base (2 ml) were added to dissolve in propanol (40 mL) , Heated to 70 C., reacted for 8 hours, solvent was recovered with the reaction solution, separated by silica gel column chromatography, washing off with chloroform-methanol (15: 1) to obtain a white solid164 mg of N6-(4-methoxy-3-hydroxy-benzyl)adenosine are obtained
  • 19
  • [ 24424-99-5 ]
  • [ 42365-68-4 ]
  • [ 161832-13-9 ]
YieldReaction ConditionsOperation in experiment
23% With sodium hydrogencarbonate; In methanol; at 20℃; for 18.0h; To a solution of 5-(aminomethyl)-2-methoxyphenol, HCl (1.1 g, 5.6 mmol) and Boc2O (2.4 g, 11 mmol) in MeOH (28 mL) was added NaHCO3 (1.9 g, 22 mmol), and the reaction mixture was stirred at rt for 18 h. The mixture was filtered, and the filtrate was concentrated. The residue was purified by flash chromatography to give 13A (0.33 g, 23 %). MS(ESI) m/z 254.0 (M+H).
 

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