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

HRID 1489588Notes

Reaction equation

HRID 1489588 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-a914b0f35a9b4ed48a5d1bcb701c6e44
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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