HCID 68950965, compound → HCID 68950992, compound

HRID 730235Notes

Reaction equation

HRID 730235 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[CH:14][C:13]=2[N+:24]([O-])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[NH2:24][C:13]1[CH:14]=[C:15]([C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)[CH:16]=[CH:17][C:12]=1[NH:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:9])=[O:10]

Participants

4

Reactant 1

HCID 68950965HCID 68950965, compound

Product 1

HCID 68950992HCID 68950992, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro-N-(2-nitro-4-pyridin-4-ylphenyl)benzene sulfonamide (0.2 mmol) in ethyl acetate (10 mL), palladium on activated carbon (10%, wet, 10 mg) was added. The reaction mixture was deaerated under vacuum for 5 min and stirred under hydrogen atmosphere (1 atm) for 30 min. The reaction mixture was filtered through a short pad of Celite, washing the pad with methanol (10 mL) and ethyl acetate (15 mL). The combined organic phase was concentrated under vacuum to give 58 mg of N-(2-amino-4-pyridin-4-ylphenyl)-4-chlorobenzene sulfonamide.

Workup

  1. filtrationThe reaction mixture was filtered through a short pad of Celite
  2. washwashing the pad with methanol (10 mL) and ethyl acetate (15 mL)
  3. concentrationThe combined organic phase was concentrated under vacuum

Sources & evidence

ORD record
ord-6730f240c939469184540132f720c97f
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

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