Tert-butyl 4-chloro-2-nitrophenyl(3-(methylsulfonyl)propyl)carbamate → Tert-butyl 2-amino-4-chlorophenyl(3-(methylsulfonyl)propyl)carbamate

HRID 1500842Notes

Reaction equation

HRID 1500842 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:16][CH2:17][CH2:18][S:19]([CH3:22])(=[O:21])=[O:20])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([N+:23]([O-])=O)[CH:3]=1>CO.[Pd]>[NH2:23][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[N:8]([CH2:16][CH2:17][CH2:18][S:19]([CH3:22])(=[O:21])=[O:20])[C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:14])[CH3:12]

Participants

4

Reactant 1

HCID 89923963Tert-butyl 4-chloro-2-nitrophenyl(3-(methylsulfonyl)propyl)carbamate

Product 1

HCID 89923659Tert-butyl 2-amino-4-chlorophenyl(3-(methylsulfonyl)propyl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-chloro-2-nitrophenyl(3-(methylsulfonyl)propyl)carbamate (360 mg, 1.45 mmol) in MeOH was added 2% Pd/C 30 mg). The reaction was degassed and refilled with H2. The mixture was stirred at RT under H2 atmosphere for 3 hrs. The catalyst was filtered off and the filtrate was concentrated to afford tert-butyl 2-amino-4-chlorophenyl(3-(methylsulfonyl) propyl)carbamate as crude product (330 mg, yield: 100%). MS obsd. (ESI+) [(M+H)+]: 363.1.

Workup

  1. customThe reaction was degassed
  2. additionrefilled with H2
  3. filtrationThe catalyst was filtered off
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ceafa2b61890414da8c5a9fe0837fae0
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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