Methanamine, N-methoxy-, hydrochloride (1:1) → 2-fluoro-N-methoxy-N-methylbenzamide

HRID 13418Notes

Reaction equation

HRID 13418 reaction equation
Cl.[CH3:2][O:3][NH:4][CH3:5].Cl.C(N=C=NCCCN(C)C)C.[F:18][C:19]1[CH:27]=[C:26]([N+]([O-])=O)[CH:25]=[CH:24][C:20]=1[C:21]([OH:23])=O>N1C=CC=CC=1>[F:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([N:4]([O:3][CH3:2])[CH3:5])=[O:23]

Participants

5

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 3026792-Fluoro-4-nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 183575562-fluoro-N-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5.79 g of N-methoxy-N-methylamine hydrochloride and 12.4 g of 1-ethyl-3-(3′-dimethylaminopropyl)-carbodiimide hydrochloride were added to a pyridine (80 ml) suspension of 10 g of 2-fluoro-4-nitrobenzoic acid, and the reaction liquid was stirred overnight at room temperature. Pyridine was evaporated away under reduced pressure, and water was added to it. The resulting deposit was taken out through filtration, washed with water, and dried to obtain the entitled compound as a pale yellow solid.

Workup

  1. customthe reaction liquid
  2. customPyridine was evaporated away under reduced pressure, and water
  3. additionwas added to it
  4. filtrationThe resulting deposit was taken out through filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-76d5f9db0bc242af8f1bbe578660f790
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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