Methyl 7-nitrobenzo[b]thiophene-2-carboxylate → Methyl 7-amino-1-benzothiophene-2-carboxylate

HRID 1986650Notes

Reaction equation

HRID 1986650 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[C:10]([N+:14]([O-])=O)=[CH:11][CH:12]=[CH:13][C:7]=2[CH:6]=1)=[O:4].[H][H]>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[C:10]([NH2:14])=[CH:11][CH:12]=[CH:13][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 57722418Methyl 7-nitrobenzo[b]thiophene-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 45089769Methyl 7-amino-1-benzothiophene-2-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

7-Nitro-benzo[b]thiophene-2-carboxylic acid methyl ester (1 g, 4.22 mmol) was suspended in EtOAc (40 mL) and a suspension of 10% Pd/C (400 mg) in 20 mL EtOAc was added. Hydrogen gas was introduced into the flask from an H2-filled balloon attached to a needle inserted through a septum. The black suspension was stirred 12 h at room temperature. After stirring 12 h, the black suspension was filtered through diatomaceous earth and the filter cake was washed several times with EtOAc. The combined filtrates were dried (MgSO4), filtered and the solvent was removed to afford 7-amino-benzo[b]thiophene-2-carboxylic acid methyl ester as a yellow solid (860 mg, 100%).

Workup

  1. additionwas added
  2. additionfilled balloon
  3. stirringAfter stirring 12 h
  4. filtrationthe black suspension was filtered through diatomaceous earth
  5. washthe filter cake was washed several times with EtOAc
  6. dry with materialThe combined filtrates were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-902c04a3c0be420d8688b6029100b3d9
Source dataset
uspto-grants-2009_06
Patent number
US07550461B2

Reaction notes

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