3-Fluorobenzoic Acid → 3-Fluoro-N-methoxy-N-methylbenzamide

HRID 1013067Notes

Reaction equation

HRID 1013067 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].Cl.[CH3:12][NH:13][O:14][CH3:15].Cl.CN(C)CCCN=C=NCC>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([N:13]([O:14][CH3:15])[CH3:12])=[O:6]

Participants

5

Reactant 3

HCID 99683-Fluorobenzoic AcidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 212657573-Fluoro-N-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-fluorobenzoic acid (140 mg, 1 mmol) and N,O-dimethylhydroxylamine hydrochloride (107 mg, 1.1 mmol) in dichloromethane (2.5 mL) was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) (211 mg, 1.1 mmol) and the mixture stirred at room temperature for 75 h. The solvents were removed under reduced pressure and the residue chromatographed using ethyl acetate-hexane (4:6) to separate the pure product (130 mg, 71%).

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue chromatographed
  3. customto separate the pure product (130 mg, 71%)

Sources & evidence

ORD record
ord-aadebac186ce4a539aa832f210d69c5e
Source dataset
uspto-grants-2011_07
Patent number
US07981900B2

Reaction notes

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