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

HRID 1907690Notes

Reaction equation

HRID 1907690 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.[H][H]>CCOC(C)=O.[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 2

HCID 59736984tert-Butyl 2-nitro-4-(thiophen-2-yl)phenylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Compound 3 was suspended in AcOEt and placed under nitrogen atmosphere; then 10% palladium on carbon (catalytic amount) was added. The reaction mixture was placed under vacuum for a few min then opened up under a balloon of hydrogen and stirred at ambient temperature for 18 h. The reaction mixture was filtered through Celite® and concentrated to give compound 4 (0.393 g, 95% yield).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a1a4ef58736b44979b724eda3b984468
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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