Acetic Acid → HCID 178518023, compound

HRID 631184Notes

Reaction equation

HRID 631184 reaction equation
[CH:1]([NH2:3])=O.C(O)(=O)C.[NH2:8][C:9]1[CH:17]=[C:16]([F:18])[C:15]([F:19])=[CH:14][C:10]=1[C:11](O)=[O:12]>O>[F:19][C:15]1[CH:14]=[C:10]2[C:9](=[CH:17][C:16]=1[F:18])[N:8]=[CH:1][N:3]=[C:11]2[OH:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 713FormamideHCID 7359652-Amino-4,5-difluorobenzoic acid

Product 1

HCID 178518023HCID 178518023, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

To a stirring mixture of formamide (10 mL) and glacial acetic acid (2.5 mL) was added 2-amino-4,5-difluorobenzoic acid (2.0 g, 11.6 mmol) and the solution stirred at 125° C. for 8 hours. After cooling to room temperature, the reaction was diluted with H2O (100 mL) and the resulting solid filtered and dried under vacuum to give 6,7-difluoro-4-hydroxyquinazoline (1.77 g, 9.7 mmol, 84%). 1H NMR (300 MHz, DMSO-d6) δ 12.49 (br s, 1H), 8.15 (s, 1H), 8.04 (dd, 1H), 7.76 (dd, 1H); LC-MS (ESI) m/z 183 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe resulting solid filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-694d17aea88d47d297485cb6c64001e5
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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