Formamide → CID 7018323

HRID 900290Notes

Reaction equation

HRID 900290 reaction equation
[NH2:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[C:4](OCC)=[O:5].C([O-])=O.[NH4+].[CH:18]([NH2:20])=O>CCOC(C)=O>[CH:10]1[C:11]([F:13])=[CH:12][C:2]2[NH:1][CH:18]=[N:20][C:4](=[O:5])[C:3]=2[CH:9]=1

Participants

5

Reactant 3

HCID 713FormamideHCID 2723923Ammonium formate2×HCID 14233600Ethyl 2-Amino-4-fluorobenzoate

Product 1

HCID 7018323CID 7018323

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of ethyl 2-amino-4-fluorobenzoate (1.73 g, 9.45 mmol) in formamide (8 mL) was added ammonium formate (0.9 g, 14 mmol). The reaction mixture was stirred at 140° C. for 24 hr, with additional ammonium formate (0.92 g, 15 mmol) at 6 hr. The reaction was dilute with EtOAc, washed with water, back-extracted with EtOAc, dried and concentrated in vacuo to give 7-fluoro-3-hydroquinazolin-4-one (2.82 g) which contains some formamide. ES-MS (M+H)+=165.

Workup

  1. washwashed with water
  2. extractionback-extracted with EtOAc
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ccd301fc2cf54e7f8e4e83ea95d9d956
Source dataset
uspto-grants-2008_04
Patent number
US07358257B2

Reaction notes

Loading…