Ethyl 4-azido-2,5-difluoro-3-difluoromethoxybenzoate → Ethyl 4-amino-2,5-difluoro-3-difluoromethoxybenzoate

HRID 1584810Notes

Reaction equation

[N:1]([C:4]1[C:14]([F:15])=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:16])[C:5]=1[O:17][CH:18]([F:20])[F:19])=[N+]=[N-]>C(O)C.C(OCC)(=O)C.[C].[Pd]>[NH2:1][C:4]1[C:14]([F:15])=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:16])[C:5]=1[O:17][CH:18]([F:19])[F:20]

Participants

Conditions

Temperature: 50 °C

Procedure

In 210 ml of ethanol and 70 ml of ethyl acetate was dissolved 13.8 g of ethyl 4-azido-2,5-difluoro-3-difluoromethoxybenzoate, and 1.38 g of 5% palladium-carbon was added to the solution, after which the resulting mixture was stirred at 50° C. for six hours under a hydrogen stream. The reaction mixture was filtered, and the filtrate obtained was concentrated under reduced pressure, to obtain 12.3 g of colorless, crystalline ethyl 4-amino-2,5-difluoro-3-difluoromethoxybenzoate.

Workup

additionwas added to the solution
filtrationThe reaction mixture was filtered
customthe filtrate obtained
concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record: ord-6b4b711cbc7a400f934b08e7fffd454a
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05935952

Reaction notes

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