Oxalyl chloride → 2-fluoro-N-methoxy-N,3-dimethylbenzamide

HRID 1294864Notes

Reaction equation

HRID 1294864 reaction equation
[F:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.[CH3:13][NH:14][O:15][CH3:16].C(Cl)(=O)C(Cl)=O>N1C=CC=CC=1>[F:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:14]([O:15][CH3:16])[CH3:13])=[O:5]

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27373792-Fluoro-3-methylbenzoic acid

Product 1

HCID 807180582-fluoro-N-methoxy-N,3-dimethylbenzamideYield 74.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepared according to Method A step A from 2-fluoro-3-methylbenzoic acid (5.0 g, 32.5 mmol), N,O-dimethylhydroxylamine hydrochloride (8.4 g, 87 mmol), oxalyl chloride (2.83 mL, 32.5 mmol) and 8 mL of pyridine to give the title compound (4.8 g) as an oil. Used as is in the next prep

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-61841e28ca6945818215ea0732a2e383
Source dataset
uspto-grants-2007_07
Patent number
US07241791B2

Reaction notes

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