HCID 58056279, compound → HCID 54192364, compound

HRID 1773505Notes

Reaction equation

HRID 1773505 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[N+:14]([O-])=O)[C:6]([N:8]([CH3:10])[CH3:9])=[O:7]>[Pd].C(O)C>[NH2:14][C:13]1[CH:12]=[CH:11][C:5]([C:6]([N:8]([CH3:10])[CH3:9])=[O:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 58056279HCID 58056279, compound

Product 1

HCID 54192364HCID 54192364, compoundYield 37.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-methoxy-N,N-dimethyl-4-nitro-benzamide (185 mg) and palladium on carbon (10%, 20 mg) in ethanol (6 mL) was stirred under hydrogen atmosphere (balloon pressure), at room temperature, overnight. The reaction mixture was filtered on a CELITE™ pad and the filtrate was concentrated under reduced pressure. The crude residue was purified by flash chromatography (DCM/MeOH, 98/2) to afford 60 mg of 4-amino-3-methoxy-N,N-dimethyl-benzamide.

Workup

  1. customat room temperature
  2. customovernight
  3. filtrationThe reaction mixture was filtered on a CELITE™ pad
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe crude residue was purified by flash chromatography (DCM/MeOH, 98/2)

Sources & evidence

ORD record
ord-0fc31567bc364a6ba879b20c6e0aa5c5
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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