Catechol → N-[2-fluoro-5-(2-hydroxyphenoxy)-4-nitrophenyl]acetamide

HRID 433724Notes

Reaction equation

[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[F:20][C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[C:24](F)=[CH:23][C:22]=1[NH:31][C:32](=[O:34])[CH3:33]>O>[F:20][C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[C:24]([O:2][C:1]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[OH:4])=[CH:23][C:22]=1[NH:31][C:32](=[O:34])[CH3:33]

Participants

Conditions

Temperature: 60 °C

Procedure

1.1 g of catechol and 2.76 g of potassium carbonate were added to 20 ml of N,N-dimethylformamide, and the mixture was heated to 60° C. Into this mixture was added dropwise a solution comprising 2.16 g of N-(2,5-difluoro-4-nitrophenyl)acetamide and 10 ml of N,N-dimethylformamide at temperatures from 65 to 70° C. The temperature of the mixture was kept for 1 hour, then, the mixture was cooled to room temperature, poured into water, extracted with ethyl acetate, and the organic layer was washed with dilute hydrochloric acid, washed with water, dried over magnesium sulfate, concentrated, and the resulted crystal was washed with t-butyl methyl ether to obtain 2.56 g of N-[2-fluoro-5-(2-hydroxyphenoxy)-4-nitrophenyl]acetamide.

Workup

additionInto this mixture was added dropwise a solution
customfrom 65 to 70° C
temperaturethe mixture was cooled to room temperature
extractionextracted with ethyl acetate
washthe organic layer was washed with dilute hydrochloric acid
washwashed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated
washthe resulted crystal was washed with t-butyl methyl ether

Sources & evidence

ORD record: ord-cf223cd60e114f12ba91a5fa83033a92
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06667413B2

Reaction notes

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