HCID 21533669, compound → HCID 21533547, compound

HRID 1657487Notes

Reaction equation

HRID 1657487 reaction equation
[CH2:1]([N:3]([CH2:31][CH3:32])[CH2:4][CH2:5][O:6][C:7]1[CH:30]=[CH:29][C:10]([N:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:12](=[O:22])[C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[CH3:2]>[Pd].C(O)C>[CH2:31]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[CH:30]=[CH:29][C:10]([N:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:12](=[O:22])[C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[CH3:32]

Participants

4

Reactant 1

HCID 21533669HCID 21533669, compound

Product 1

HCID 21533547HCID 21533547, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4.69 g. of 4'-(2diethylaminoethoxy)-4-nitro-N-phenylbenzanilide (Example 20) in 300 ml. of ethanol was hydrogenated in the presence of 1 g. of palladium-on-carbon catalyst. The catalyst was removed by filtration, the filtrate evaporated to remove the solvent, and the residue recrystallized from isopropyl alcohol-ether and ethanol-ether to give 4'-(2-diethylaminoethoxy)-4-amino-N-phenylbenzanilide, yellow solid, m.p. 174.5°-178.5°C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated
  3. customto remove the solvent
  4. customthe residue recrystallized from isopropyl alcohol-ether and ethanol-ether

Sources & evidence

ORD record
ord-382c161758f84ea0af68c22a4b78d8e6
Source dataset
uspto-grants-1976_06
Patent number
US03960886

Reaction notes

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