Ethyl 5-bromo-4-nitrothiophene-2-carboxylate → Ethyl 4-aminothiophene-2-carboxylate

HRID 59739Notes

Reaction equation

HRID 59739 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][C:3]=1[N+:12]([O-])=O>CO>[NH2:12][C:3]1[CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[S:6][CH:2]=1

Participants

3

Reactant 1

HCID 18957942Ethyl 5-bromo-4-nitrothiophene-2-carboxylate

Product 1

HCID 22418292Ethyl 4-aminothiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 5-bromo-4-nitrothiophene-2-carboxylate (Int. 40) (500 mg, 1.785 mmol) in MeOH (35 ml) was hydrogenated in a continuous-flow hydrogenation reactor (H-Cube apparatus) (flow rate: 1.0 ml/min, Temp: 50° C., H2 pressure: 20 bar). The solvent was evaporated affording ethyl 4-aminothiophene-2-carboxylate (Int. 41) which was used without any additional purification (350 mg, MS/ESI+172.1 [MH]+).

Workup

  1. custom(H-Cube apparatus) (flow rate: 1.0 ml/min, Temp: 50° C., H2 pressure: 20 bar)
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-44f7fc3761c84411979b453cccd8f376
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Reaction notes

Loading…