3,4-Dimethoxy-6-nitrobenzamide → 2-Amino-4,5-dimethoxybenzamide

HRID 2292361Notes

Reaction equation

HRID 2292361 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([N+:14]([O-])=O)=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([NH2:8])=[O:7]>[Pd].C(O)C>[NH2:14][C:9]1[CH:10]=[C:11]([O:12][CH3:13])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[C:6]([NH2:8])=[O:7]

Participants

4

Reactant 1

HCID 27361933,4-Dimethoxy-6-nitrobenzamide

Product 1

HCID 108672362-Amino-4,5-dimethoxybenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.5 g of 10% palladium on charcoal was added to a suspension of 7.5 g (33 mmol) of 3,4-dimethoxy-6-nitrobenzamide in 200 ml of ethanol, and the mixture was hydrogenated for 1 hour under a pressure of 45 psi. After removal of the catalyst, the filtrate was concentrated in vacuo and the residue triturated with 80 ml of ether/petroleum ether 1:1. The crystals were filtered, washed with petroleum ether and dried in vacuo; yield: 6.15 g, melting point 142.7° C.

Workup

  1. customAfter removal of the catalyst
  2. concentrationthe filtrate was concentrated in vacuo
  3. customthe residue triturated with 80 ml of ether/petroleum ether 1:1
  4. filtrationThe crystals were filtered
  5. washwashed with petroleum ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-756c2b97e01f407b8aa6eb45e665402e
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

Loading…