tert-Butyl 2-nitro-4-(thiophen-2-yl)phenylcarbamate → tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

HRID 62666

Reaction equation

HRID 62666 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH:7]=[CH:6][C:5]=1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([O-])=O>C(O)C.CO.[Pd]>[NH2:1][C:4]1[CH:9]=[C:8]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH:7]=[CH:6][C:5]=1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21]

Participants

5

Reactant 1

HCID 59736984tert-Butyl 2-nitro-4-(thiophen-2-yl)phenylcarbamate

Product 1

HCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamateYield 69.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (2-nitro-4-(thiophen-2-yl)phenyl)carbamate (2 g, 6.2 mmol, 1.0 eq.) in ethanol (20 mL) and methanol (20 mL) was added 10% Pd/C (0.66 g, 0.1 eq.). The reaction mixture was stirred 12 h under a hydrogen atmosphere. The reaction was filtered and the filtrate was concentrated under reduced pressure to give tert-butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate (1.25 g, 69% yield) as an off-white solid.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1d4ead8e26a1418982cbebc4494fe31e
Source dataset
uspto-grants-2016_09
Patent number
US09447030B2

Linked notes

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