N-Methyl-4-nitroaniline → N-Methyl-N-(4-nitrophenyl)butyramide

HRID 1983568Notes

Reaction equation

HRID 1983568 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[CH3:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:7][N:8]([C:9]1[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=1)[C:1](=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 7483N-Methyl-4-nitroanilineHCID 8471TriethylamineHCID 8855Butyryl chloride2×

Product 1

HCID 68840696N-Methyl-N-(4-nitrophenyl)butyramideYield 76%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of butyryl chloride (0.770 g, 7.23 mmol) in chloroform ( 15 mL) was added N-methyl-4-nitroaniline and triethylamine (1.2 mL, 8.6 mmol). After overnight stirring, additional butyryl chloride (0.40 mL, 3.9 mmol) was added and the reaction was refluxed for 2-3 hours. The reaction was concentrated and the residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was combined with a second ethyl acetate extract, dried (sodium sulfate) and concentrated. The resulting dirty yellow oil was purified by flash chromatography over silica (methylene chloride/methanol) to afford 1.11 g (76%) of product as a pale yellow solid: 1H NMR (CDCl3) δ 8.30 (d, J=8.9 Hz, 1H), 7.40 (d, J=8.9 Hz, 1H), 3.34 (s, 3H), 2.18 (t, J=7.5 Hz, 2H), 1.71-1.59 (m, 2H), 0.88 (t, J=7.6Hz,

Workup

  1. temperaturethe reaction was refluxed for 2-3 hours
  2. concentrationThe reaction was concentrated
  3. customthe residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  4. extractionextract
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. customThe resulting dirty yellow oil was purified by flash chromatography over silica (methylene chloride/methanol)

Sources & evidence

ORD record
ord-cceb2c32e7b745a7a63b8e6593f10b4b
Source dataset
uspto-grants-2009_06
Patent number
US07541466B2

Reaction notes

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