[1,1'-Biphenyl]-4-sulfonamide, N-(4-hydroxybutyl)-2'-nitro- → [1,1'-Biphenyl]-4-sulfonamide, 2'-amino-N-(4-hydroxybutyl)-

HRID 2425145Notes

Reaction equation

HRID 2425145 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-])=O)=[CH:12][CH:11]=1)(=[O:9])=[O:8]>CO.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH2:22])=[CH:12][CH:11]=1)(=[O:9])=[O:8]

Participants

4

Reactant 1

HCID 11695987[1,1'-Biphenyl]-4-sulfonamide, N-(4-hydroxybutyl)-2'-nitro-

Product 1

HCID 11702508[1,1'-Biphenyl]-4-sulfonamide, 2'-amino-N-(4-hydroxybutyl)-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2′-Nitrobiphenyl-4-sulfonic acid-(4-hydroxybutyl)-amide (0.5 g) was dissolved in methanol (50 mL). 10% Pd/C (0.5 g) was added and the mixture stirred under hydrogen for 4 hours. The mixture was filtered through celite and evaporated to a brown oil. Column chromatography gave a clear oil, crystallised from ether/petrol to give a white powder. δC (DMSO, 62.9 MHz): 25.9, 29.6, 42.6, 60.3, 115.6, 116.8, 124.1, 126.8, 128.8, 129.3, 129.9, 138.6, 143.8 and 145.2.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated to a brown oil
  3. customColumn chromatography gave a clear oil
  4. customcrystallised from ether/petrol
  5. customto give a white powder

Sources & evidence

ORD record
ord-d80ca809cda04ef69268b2f2e88c0f50
Source dataset
uspto-grants-2011_06
Patent number
US07964643B2

Reaction notes

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