2',3'-Dimethyl-3-nitrobenzanilide → 3-amino-N-(2,3-dimethylphenyl)benzamide

HRID 1780804Notes

Reaction equation

HRID 1780804 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:11]=1[CH3:17])=[O:8])([O-])=O.[H][H]>CO.O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:11]=1[CH3:17])=[O:8]

Participants

6

Reactant 2

HCID 8165712',3'-Dimethyl-3-nitrobenzanilideHCID 178418361HCID 178418361, compound

Product 1

HCID 64565863-amino-N-(2,3-dimethylphenyl)benzamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1 (1 g) in 70 mL methanol and 30 mL of tetrahydrofuran was added 10% Pd/C (0.2 g) under nitrogen atmosphere. Hydrogen was applied to the mixture at 60 psi for 16 h. The mixture was filtered and concentrated in vacuo to obtain the product. NMR (300 MHz, CDCl3) δ 7.71 (1H, s), 7.55 (1H, d, J=9 Hz), 7.23 (1H, t, J=9 Hz), 7.19 (1H, s), 7.14 (1H, t, J=9 Hz), 7.04 (1H, d, J=9 Hz), 6.82 (1H, d, J=9 Hz), 3.84 (2H, b), 2.32 (3H, s), 2.20 (2H, s).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customto obtain the product

Sources & evidence

ORD record
ord-cbf59ca0dd2742b38f7a171f2f89ecae
Source dataset
uspto-grants-1997_05
Patent number
US05631280

Reaction notes

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