HCID 21473553, compound → 178672-23-6

HRID 2294137Notes

Reaction equation

HRID 2294137 reaction equation
[CH3:1][N:2]([CH3:15])[C:3](=[O:14])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[N+:11]([O-])=O>[Pd].C(O)C>[NH2:11][C:5]1[CH:6]=[CH:7][C:8]([CH3:10])=[CH:9][C:4]=1[C:3]([N:2]([CH3:15])[CH3:1])=[O:14]

Participants

4

Reactant 1

HCID 21473553HCID 21473553, compound

Product 1

HCID 10845051178672-23-6Yield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

A mixture of N,N,5-trimethyl-2-nitrobenzamide (11 g, 52.8 mmol) and 5% palladium on carbon (1 g) in 100 mL of ethanol was stirred under a hydrogen atmosphere for 18 hours. Additional 5% palladium on carbon (1 g) was added and the mixture was stirred for approximately 8 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified on silica gel by flash chromatography eluting with 4% ethanol/methylene chloride to give 2-amino-N,N,5-trimethylbenzamide (8 g, 44.9 mmol), m.p. 98°-99° C.

Workup

  1. stirringthe mixture was stirred for approximately 8 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified on silica gel by flash chromatography
  5. washeluting with 4% ethanol/methylene chloride

Sources & evidence

ORD record
ord-e10ec319336c4b15a553548d883b0148
Source dataset
uspto-grants-1997_11
Patent number
US05688795

Reaction notes

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