Methylamine → N-methyl-3-nitrobenzamide

HRID 1169201Notes

Reaction equation

HRID 1169201 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[CH3:13][NH2:14]>O1CCCC1.C(OCC)(=O)C>[CH3:13][NH:14][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 8495Benzoyl chloride, 3-nitro-

Product 1

HCID 221964N-methyl-3-nitrobenzamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In a dry flask 3-nitrobenzoyl chloride (7.00 g, 37.7 mmol) was dissolved in tetrahydrofuran (300 mL) and methylamine (41.5 mL of a 2.0 M solution in tetrahydrofuran, 82.9 mmol) was added. The reaction mixture was stirred for 2 hours. The reaction mixture was diluted with ethyl acetate (500 mL) and extracted with water three times (100 mL). The organic layer was dried with sodium sulfate, filtered, and concentrated in vacuo. The crude solid (6.38 g, 94%) was used with further purification. 1H NMR (300 MHz, CDCl3), δ: 8.84 (bs, 1H), 8.67 (m, 1H), 8.37 (dd, J=8, J′=2, 1H), 8.28 (d, J=7, 1H), 7.78 (dd, J=8, J′=7, 1H), 2.83 (m, 3H). MS (ESI), m+/z: (M+H)+=181.

Workup

  1. extractionextracted with water three times (100 mL)
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude solid (6.38 g, 94%) was used with further purification

Sources & evidence

ORD record
ord-22341ac67c0e4b0c80bfd732e712e111
Source dataset
uspto-grants-2003_09
Patent number
US06627629B2

Reaction notes

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