Isopropanol → 4-(6-Bromo-7-methyl-8-nitroquinazolin-4-ylamino)benzonitrile

HRID 1042257Notes

Reaction equation

HRID 1042257 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[CH3:12])[N:8]=[CH:7][N:6]=[C:5]2Cl.[NH2:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1.CC(O)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[CH3:12])[N:8]=[CH:7][N:6]=[C:5]2[NH:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 133964-AminobenzonitrileHCID 589422476-Bromo-4-chloro-7-methyl-8-nitroquinazoline

Product 1

HCID 687269114-(6-Bromo-7-methyl-8-nitroquinazolin-4-ylamino)benzonitrileYield 72.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 6-bromo-4-chloro-7-methyl-8-nitroquinazoline (211 mg, 0.70 mmol) and 4-aminobenzonitrile (208 mg, 1.76 mmol) in toluene (25 mL) was refluxed overnight. i-PrOH (25 mL) was added and the mixture was refluxed for 5 h. After cooling to rt the precipitate was filtered and washed with i-PrOH to give 4-(6-bromo-7-methyl-8-nitroquinazolin-4-ylamino)benzonitrile (195 mg, 72%). MS (ESI, pos. ion) m/z: 384 [M+H]+

Workup

  1. temperaturewas refluxed overnight
  2. temperaturethe mixture was refluxed for 5 h
  3. filtrationwas filtered
  4. washwashed with i-PrOH

Sources & evidence

ORD record
ord-e07e1c009c9140eeb4a7cc29af268989
Source dataset
uspto-grants-2013_10
Patent number
US08557830B2

Reaction notes

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