3-Bromoaniline → N-(3-Bromophenyl)-6-nitroquinazolin-4-amine

HRID 1068964Notes

Reaction equation

HRID 1068964 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C([C:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=1[N:20]=[CH:21][N:22]([CH3:24])C)#N>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:24]2[C:11]3[C:12](=[CH:13][CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=3)[N:20]=[CH:21][N:22]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 10900084N'-(2-cyano-4-nitrophenyl)-N,N-dimethylmethanimidamide

Product 1

HCID 5328041N-(3-Bromophenyl)-6-nitroquinazolin-4-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
148 °C

Procedure

A solution of 23.74 mL of 3-bromo aniline and 40.5 g N′-(2-cyano-4-nitrophenyl)-N,N-dimethylformamidine in 100 mL of glacial acetic acid was stirred and heated in an oil bath at 148° C. for 1.5 hours. On cooling, filtration of the resulting solid gives a quantitative yield of N-(3-bromophenyl)-6-nitro-4-quinazolinamine: mp=267-270° C.; mass spectrum (m/e): 345.

Workup

  1. temperatureOn cooling
  2. filtrationfiltration of the resulting solid

Sources & evidence

ORD record
ord-e151269b24f2472798785ba3fc238e61
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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