Methylamine → N-Methyl-4-nitrobenzamide

HRID 395367Notes

Reaction equation

HRID 395367 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:13][NH2:14].CCOC(C)=O>C1COCC1>[CH3:13][NH:14][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 85024-Nitrobenzoyl chlorideHCID 8857Ethyl Acetate

Product 1

HCID 347921N-Methyl-4-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Nitrobenzoyl chloride (7.00 g, 38 mmol, 1 eq) was dissolved in 50 ml of THF and added to a 2.0 M solution of methylamine in THF (41.5 ml, 83 mmol, 2.2 eq.) at 0° C. Worked up after 3 hours by adding EtOAc and rinsing 3× with 1N NaOH, 1× with brine. The organic layer was dried over MgSO4, then stripped to obtain 2.25 g of off-white solids as product. NMR (300 MHz, DMSO-d6) δ 8.80 (m, 1H), 8.33 (d, 2H, J=7 Hz), 8.06 (d, 2H, J=7 Hz). 2.86 (d, 3H, J=7 Hz).

Workup

  1. washrinsing 3× with 1N NaOH, 1× with brine
  2. dry with materialThe organic layer was dried over MgSO4

Sources & evidence

ORD record
ord-374f943694a44131a1d1ea3d490082c3
Source dataset
uspto-grants-2003_08
Patent number
US06605623B1

Reaction notes

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