4-(4-Dimethylaminosulfonylbenzyl)-nitrobenzene → 4-(4-Dimethylaminosulfonylbenzyl)-phenylamine

HRID 634812Notes

Reaction equation

HRID 634812 reaction equation
[CH3:1][N:2]([CH3:22])[S:3]([C:6]1[CH:21]=[CH:20][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4]>C(OCC)(=O)C.[Pd]>[CH3:22][N:2]([CH3:1])[S:3]([C:6]1[CH:21]=[CH:20][C:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:5]

Participants

4

Reactant 1

HCID 218769584-(4-Dimethylaminosulfonylbenzyl)-nitrobenzene

Product 1

HCID 218770384-(4-Dimethylaminosulfonylbenzyl)-phenylamineYield 102.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-(4-Dimethylaminosulfonylbenzyl)-nitrobenzene (311 mg) was dissolved in ethyl acetate and hydrogenated at 40 psi using a 10% palladium on carbon catalyst for 2 hours. The mixture was filtered, and solvents evaporated to give 4-(4-dimethylaminosulfonylbenzyl)-phenylamine as a white solid (288 mg, 99%).

Workup

  1. customfor 2 hours
  2. filtrationThe mixture was filtered
  3. customsolvents evaporated

Sources & evidence

ORD record
ord-be4ab456c997421a89d790a767c9eab7
Source dataset
uspto-grants-2001_02
Patent number
US06184242B2

Reaction notes

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