Formamide → 6-Nitroquinazolin-4-amine

HRID 2296421Notes

Reaction equation

HRID 2296421 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].[CH:19]([NH2:21])=O.CN(C)C=O>O>[NH2:5][C:4]1[C:3]2[C:2](=[CH:9][CH:8]=[C:7]([N+:10]([O-:12])=[O:11])[CH:6]=2)[N:1]=[CH:19][N:21]=1

Participants

6

Reactant 4

HCID 713FormamideHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 285322-Amino-5-nitrobenzonitrile

Product 1

HCID 130604546-Nitroquinazolin-4-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-amino-5-nitrobenzonitrile (48.9 g), anhydrous potassium carbonate (45.6 g), formamide (240 ml) and N,N-dimethylformamide (200 ml) was stirred for 50 minutes at 150° C. and then cooled to ambient temperature. To the resultant mixture was added a small volume of water with stirring. Precipitated crystals were separated by filtration, washed three times with water and dried under reduced pressure to give crystalline 4-amino-6-nitroquinazoline (50.1 g).

Workup

  1. temperaturecooled to ambient temperature
  2. stirringwith stirring
  3. customPrecipitated crystals
  4. customwere separated by filtration
  5. washwashed three times with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-4891c4d5707342abbbce144d974cdc00
Source dataset
uspto-grants-1984_01
Patent number
US04429126

Reaction notes

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