Triethylamine → Ethyl 4-(methylamino)-3-nitrobenzoate

HRID 1498888Notes

Reaction equation

HRID 1498888 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH2:16]([N:18](CC)CC)C.CN.CO>CO>[CH3:16][NH:18][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21277355Ethyl 4-fluoro-3-nitrobenzoateHCID 57454252Monomethylamine methanol

Product 1

HCID 12493881Ethyl 4-(methylamino)-3-nitrobenzoateYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 4-fluoro-3-nitrobenzoate (10.0 g, 46.9 mmol) prepared in the Step 1-1-1 was dissolved in methanol (40 ml), and triethylamine (10 ml, 70.4=01) was added thereto. Under an ice cooling, a 40% methylamine-methanol solution (5.50 g, 70.4 mmol) was added to the mixture. After the resulting mixture was stirred for one hour under an ice cooling, ice water was added thereto. The precipitate was separated by filtration and washed with water. The washed product was subjected to through circulation drying overnight to give the title compound (10.4 g, 99%) as a yellow powder.

Workup

  1. customThe precipitate was separated by filtration
  2. washwashed with water
  3. customdrying overnight

Sources & evidence

ORD record
ord-71f9b73d917441e1b719d3c8624b013c
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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