Potassium Hydroxide → 7-Amino-4-(3-bromoanilino)-6-nitroquinazoline

HRID 1358271Notes

Reaction equation

HRID 1358271 reaction equation
C([NH:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[CH:17]=3)=[N:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[N+:23]([O-:25])=[O:24])(=O)C.[OH-].[K+]>CO.O>[NH2:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[CH:17]=3)=[N:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[N+:23]([O-:25])=[O:24]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 53282177-Acetamido-4-(3-bromoanilino)-6-nitroquinazoline

Product 1

HCID 53282147-Amino-4-(3-bromoanilino)-6-nitroquinazolineYield 87.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 7-acetamido-4-(3-bromoanilino)-6-nitroquinazoline (1.50 g, 3.73 mmol) and KOH (2 g) in MeOH (190 mL) and H2O (10 mL) is heated under reflux for 30 min, and the solvent volume is reduced to give 7-amino-4-(3-bromoanilino)-6-nitroquinazoline (1.17 g, 87%). 1H NMR (DMSO) δ10.17 (1H, brs), 9.43 (1H, s), 8.43 (1H, s), 8.15 (1H,m brs), 7.86 (1H, d, J=7.1 Hz), 7.42 (2H, brs), 7.40-7.31 (2H, m) , 7.12 (1H, s).

Workup

  1. temperatureunder reflux for 30 min

Sources & evidence

ORD record
ord-44b322aeb81040729ff9423b0329e70c
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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