Ammonium Chloride → 4-Amino-N-methylbenzamide

HRID 1665634Notes

Reaction equation

HRID 1665634 reaction equation
[Cl-].[NH4+].[CH3:3][NH:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1>O.CO.C1COCC1.[Zn]>[NH2:12][C:9]1[CH:8]=[CH:7][C:6]([C:5]([NH:4][CH3:3])=[O:15])=[CH:11][CH:10]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 347921N-Methyl-4-nitrobenzamide

Product 1

HCID 2355164-Amino-N-methylbenzamideYield 86.5%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ammonium chloride (29.6 g, 55.4 mmol) in water (200 mL) and methanol (200 mL) was added to a solution of N-methyl-4-nitro-benzamide (10 g, 55.4 mmol) in THF (160 mL). Zinc powder (29 g, 44.4 mmol) was added portion wise and the mixture stirred for 15 minutes. The reaction mixture was filtered over celite, the filtrate was then concentrated and extracted with ethyl acetate. The organics were washed with brine solution, dried over Na2SO4 and concentrated to afford 7.2 g (86%) of 4-amino-N-methyl-benzamide. 1H NMR: (DMSO-d6): δ 7.9 (s, 1H), 7.6 (d, 2H), 6.5 (d, 2H), 5.6 (s, 2H), 2.7 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. concentrationthe filtrate was then concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organics were washed with brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bc2676b84f9640879242937b7a7a6eb7
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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