Methylamine → HCID 21884189, compound

HRID 722415Notes

Reaction equation

HRID 722415 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5](O)=[O:6].Cl.[CH3:15][N:16](C)CCCN=C=NCC.CN>C(Cl)Cl.CO>[CH3:15][NH:16][C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([F:1])[CH:3]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 2306533-Fluoro-4-nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 21884189HCID 21884189, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-fluoro-4-nitrobenzoic acid (4.0 g, 21.6 mmol) and EDC (1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride) (4.36 g, 28.1 mmol) in methylene chloride (100 mL) was added methylamine (11.3 mL of a 2 M solution in MeOH, 22.7 mmol) and the solution was stirred at room temperature overnight. The solution was washed with 1 N HCl, dried over MgSO4 and concentrated to a solid. The solid was triturated with butyl chloride and collected by filtration to give the N-methyl-3-fluoro-4-nitrobenzamide (3.81 g, 96%).

Workup

  1. washThe solution was washed with 1 N HCl
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated to a solid
  4. customThe solid was triturated with butyl chloride
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-420e3707168b4cf1a7b3897881970a74
Source dataset
uspto-grants-2006_11
Patent number
US07138420B2

Reaction notes

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