N-(4-Nitrobenzyl)cyclopropanesulfonamide → N-(4-Aminobenzyl)cyclopropanesulfonamide

HRID 550779Notes

Reaction equation

HRID 550779 reaction equation
[CH:1]1([S:4]([NH:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([S:4]([NH:7][CH2:8][C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 66910210N-(4-Nitrobenzyl)cyclopropanesulfonamide

Product 1

HCID 64552598N-(4-Aminobenzyl)cyclopropanesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-Cyclopropylsulfonyl-4-nitrobenzylamine was dissolved in methanol (50 mL) and to the solution was added 10% Pd—C. The reaction mixture was reacted under hydrogen atmosphere (˜40 psi) for 1 h. The catalyst was filtered off over celite and washed with methanol (1 L) and water (10 mL). The filtrate was evaporated to give N-cyclopropylsulfonyl-4-aminobenzylamine. 1H NMR (DMSO-d6): δ 0.87 (m, 4H), 2.37 (m, 1H), 3.96 (d, J=6.0 Hz, 2H), 4.99 (br, 2H), 6.49 (d, J=8.1 Hz, 2H), 6.96 (d, J=8.4 Hz, 2H), 7.33 (t, J=6.0 Hz, 1H).

Workup

  1. customThe reaction mixture was reacted under hydrogen atmosphere (˜40 psi) for 1 h
  2. filtrationThe catalyst was filtered off over celite
  3. washwashed with methanol (1 L) and water (10 mL)
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-33d5b359f8f94ce39d05b5b043aa8aa2
Source dataset
uspto-grants-2011_05
Patent number
US07947698B2

Reaction notes

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