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Chemistry
Heterocyclic Building Blocks
Quinazolines
4,7-Dichloro-6-nitroquinazoline
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
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Chlorides Nitroes

[ CAS No. 162012-71-7 ] 4,7-Dichloro-6-nitroquinazoline

Cat. No.: A826814
Chemical Structure| 162012-71-7
Chemical Structure| 162012-71-7
 Structure of 162012-71-7 * Storage: Inert atmosphere,2-8°C
Purity Size Price USA Stock *0-1 Day Global Stock *5-7 Days Quantity
98% 100mg $470.00 Inquiry Inquiry
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* Storage: Inert atmosphere,2-8°C

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Product Details of [ 162012-71-7 ]

CAS No. :162012-71-7 MDL No. :MFCD15528783
Formula : C8H3Cl2N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 244.03 Pubchem ID :-
Synonyms :

Safety of [ 162012-71-7 ]

Signal Word:Warning Class:
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 UN#:
Hazard Statements:H302-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 162012-71-7 ]

* 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 [ 162012-71-7 ]

[ 162012-71-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 53449-14-2 ]
  • [ 162012-71-7 ]
YieldReaction ConditionsOperation in experiment
95% With thionyl chloride; In N,N-dimethyl-formamide; for 24h;Reflux; 3,4-Dihydro-6-nitro-7-chloro-4-oxoquinazoline (2 g) was placed in a 100 ml Erlenmeyer flask,After adding 40 ml of thionyl chloride and 1 drop of DMF at room temperature,Heated to reflux for 24 hours, most of the thionyl chloride was distilled off,Ice water was added, filtered and dried to give 4-chloro-6-nitro-7-chloroquinazoline (2.05 g) in 95% yield.
With trichlorophosphate; for 2h;Heating / reflux; 4.00g of the above crystalline 6-nitro-7-chloro-quinazolone was refluxed with 15 mL of phosphoryl chloride for 2h, then the reaction mixture was poured into ice water, filtered and dried to obtain the intermediate 6-nitro-4,7-dichloro- quinazoline;
With trichlorophosphate; for 2h;Heating / reflux; 4.00 g of the above crystalline 6-nitro-7-chloro-quinazolone was refluxed with 15 mL of phosphoryl chloride for 2 h, then the reaction mixture was poured into ice water, filtered and dried to obtain the intermediate 6-nitro-4,7-dichloro-quinazoline; The intermediate was dissolved into 30 mL of isopropanol, and 3.00 g of 3-chloro-4-(m-fluoro-benzyloxy)-aniline was added. The reaction mixture was reacted under reflux for 2 h and a lot of solid was deposited, which was filtered and dried under vacuum to obtain the solid product of 6-nitro-7-chloro-4-amino substituted quinazoline (3.83 g).
With phosphorus pentachloride; trichlorophosphate; In tetrachloromethane; for 2h;Reflux; 7-Chloro-6-nitro-quinazolin-4-one (1.002 g, 4.44 mmol), phosphorous oxychloride (11.5 g, 7.51 mmol) andphosphorous pentachloride (1.62 g, 7.74 mmol) were refluxed for 2 hours and the reaction mixture was concentrated invacuo to a residue which was triturated with toluene and then again with chloroform and dried in vacuo to afford crude4,7-dichloro-6-nitro-quinazoline. This was dissolved in 35 mL of isopropyl alcohol and 3-ethynylaniline (639 mg, 5.45mmol) and refluxed for 3 hours. The cooled reaction mixture was filtered to afford the title product as a solid which waswashed with 10 mL of isopropyl alcohol and dried in vacuo at 70C, 1.055 g (66%); mp 230.8-232.6C.
With triethylamine; trichlorophosphate; In acetonitrile; at 80℃; 10g of compound BB3 placed 40ml of acetonitrile, followed by adding 8.3 g of phosphorus oxychloride, 5.4 g of triethylamine, and the reaction was heated to 80 C until the reaction was complete as monitored by TLC.
With thionyl chloride; In N,N-dimethyl-formamide; for 2h;Reflux; The above-obtained 6-nitro-7-chloro-3H-quinazolin-4-one (9.0g (40.0mmol) was added to a 9011S0C12 solution and then 0.9 mL of DMF was added,Reflux stirring 2h,The solution gradually became dark yellow clear,The reaction was quenched, cooled to room temperature and excess S0C12 evaporated to give 4,7-dichloro-6-nitroquinazoline as a yellow solid. The yellow solid was crushed and added50 mL of petroleum ether. The petroleum ether was distilled off under reduced pressure and the procedure was repeated twice with petroleum ether to remove the residual S0C12 to obtain a yellow solid.The yellow solid was transferred to a three-necked flask without purification, and 3-methylaniline (4.71g, 44.0mmol), isopropanol (17101)Reflux stirring 2h, precipitation of solid, cooling to room temperature, collecting solid, washing with isopropyl alcohol, dry, yellow solid 6-nitro-7-Chloro-4- (3-methylanilino) quinazoline in a yield of 54.7%.
Examples; Example 1, synthesis of the compound: 8-allyl-4-(3-chloro-4-methoxy-benzylamino)-6-nitro-quinazolin-7-ol; 1) Synthesis of compound 5; A starting material 3 (5.7 g, 25.3 mmol) was dissolved in thionyl chloride(110.3 ml) and dimethylformamide (three drops) was added thereto at room <n="30"/>temperature. The mixture was stirred at reflux for 17 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. The solvent was removed by distillation under reduced pressure. The resulting mixture was diluted with ethyl acetate and washed with a saturated NaHCO3 solution and brine. The organic layer was dried over anhydrous sodium sulfate, distilled under reduced pressure to remove the solvents and dried under vacuum to obtain a compound. The compound and 3-chloro-4-methoxy-benzylamine (5.61 g, 27 mmol) were dissolved in isopropyl alcohol (50 ml) and triethylamine (7.56 ml, 54 mmol) was then added thereto. The resulting mixture was stirred at room temperature for 17 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane and washed with 5% citric acid, 1 N sodium hydroxide, water and brine. The mixture was dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The resulting residue was eluted with dichloromethane/hexane (4 :1) to yield a compound 5 (7.8 g, 81%, 2 steps) as a yellow solid. 5 1H NMR (CD3OD, 400 MHz) delta 8.413 (s, IH), 7.907 (d, J = 2.21 Hz,IH), 7.709 (d, J = 8.92 Hz, IH), 7.637 (dd, J = 8.91, 2.28 Hz, IH), 7.408 (d,J = 2.10 Hz, IH), 7.306 (dd, J = 8.54, 2.21 Hz, IH), 7.006 (d, J = 8.44 Hz, 0IH), 4.780 (s, 2H), 3.846 (s, 3H), 3.051 (s, 3H). MS (ESI) m/z 393 (M+ + 1)

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 267 - 276
[2]Patent: CN107674059,2018,A .Location in patent: Paragraph 0301; 0302; 0303; 0304
[3]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 545 - 548
[4]Chemical and Pharmaceutical Bulletin,2002,vol. 50,p. 1073 - 1080
[5]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 383 - 391
[6]Patent: EP1990337,2008,A1 .Location in patent: Page/Page column 11
[7]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6279 - 6282
[8]Patent: US2008/300248,2008,A1 .Location in patent: Page/Page column 7
[9]Medicinal Chemistry Research,2013,vol. 22,p. 4096 - 4109
[10]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 7988 - 7998
[11]Patent: EP2163546,2016,B1 .Location in patent: Paragraph 0121
[12]Patent: CN103570738,2016,B .Location in patent: Paragraph 0303; 0304; 0308
[13]Patent: CN103382182,2016,B .Location in patent: Paragraph 0506; 0507; 0510; 0511
[14]Patent: WO2008/20711,2008,A1 .Location in patent: Page/Page column 23; 28-29
  • 2
  • [ 5900-59-4 ]
  • [ 162012-71-7 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 545 - 548
  • 3
  • [ 2338-18-3 ]
  • [ 162012-71-7 ]
  • C17H14ClN5O2 [ No CAS ]
  • C17H14ClN5O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
140 mg; 35 mg With triethylamine; In isopropyl alcohol; at 50℃; for 8h; A mixture of SP-0011507-064 (300 mg, 1.23 mmol), 2,3-dihydro-1H-indene-2,5- diamine (200 mg, 1.35 mmol) and triethylamine (0.53 mL, 3.69 mmol) in isopropyl alcohol (30 mL) was heated to 50 C for 8 h. The mixture was cooled down and excess of isopropyl alcohol was removed by rotary evaporation. The resulting mixture was evaporated and the residue was purified by Prep-HPLC to give A29-090 (140 mg) and A29-091 (35 mg).A29-090 LC-MS 356 (M+H), purity 100% (UV 214 nm); ?H NMR (400 MHz, DMSO-d6) oe 9.30 (s, 1 H), 8.95 (d, J = 6.4 Hz, 1 H), 8.63 (s, 1 H), 7.98 (s, 1 H), 6.89 (d, J = 8.0 Hz, 1 H), 6.48 (s, 1 H), 6.40 (d J = 7.6 Hz, 1 H), 4.98-4.92 (m, 1 H), 4.87 (s, 2 H), 3.33-3.18 (m, 2 H), 2.93-2.84 (m, 2 H).A29-091 LC-MS 356 (M+H), purity 100% (UV 214 nm); ?H NMR (400 MHz,DMSO-d6) oe 8.87 (s, 1 H), 8.63 (d, J = 8.4 Hz, 1 H), 8.57 (s, 1 H), 7.83 (d, J = 8.4 Hz, 1 H),6.89 (d J = 6.0 Hz,1 H), 6.45 (s, 1 H), 6.40 (d, J = 7.6 Hz, 1 H), 4.98-4.92 (m, 1 H), 4.87 (s,2 H), 3.25-3.20 (m, 2 H), 2.94-2.85 (m, 2 H).
Reference： [1]Patent: WO2014/145512,2014,A2 .Location in patent: Page/Page column 112; 113

Tags: 162012-71-7 synthesis path| 162012-71-7 SDS| 162012-71-7 COA| 162012-71-7 purity| 162012-71-7 application| 162012-71-7 NMR| 162012-71-7 COA| 162012-71-7 structure

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• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling
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