Methyl 6-nitro-1-benzothiophene-2-carboxylate → Methyl 6-aminobenzo[b]thiophene-2-carboxylate

HRID 500675Notes

Reaction equation

HRID 500675 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=[CH:13][C:7]=2[CH:6]=1)=[O:4]>CN(C=O)C.[Pd]>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([NH2:14])[CH:12]=[CH:13][C:7]=2[CH:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 23626901Methyl 6-nitro-1-benzothiophene-2-carboxylate

Product 1

HCID 15557582Methyl 6-aminobenzo[b]thiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 6-nitro-benzo[b]thiophene-2-carboxylic acid methyl ester (3.9 g, 15.8 mmol) in DMF (120 mL) was added 10% Pd/C (700 mg, 10 wt %). The reaction was charged with H2, degassed and refilled with hydrogen three times. The slurry was stirred at RT for 4 days at balloon pressure, then filtered through a plug of Celite, and solvent was removed under reduced pressure. The solid was washed with EtOAc, and filtered to yield the desired amine. 1H NMR (CDCl3) δ 7.92 (s, 1H), 7.65 (d, J=8.4 Hz, 1H), 7.08 (s, 1H), 6.78 (d, J=8.4 Hz, 1H), 3.92 (s, 3H). MS (EI): cal'd (ME) 208.04, exp (MH+) 208.1.

Workup

  1. additionThe reaction was charged with H2
  2. customdegassed
  3. additionrefilled with hydrogen three times
  4. filtrationfiltered through a plug of Celite, and solvent
  5. customwas removed under reduced pressure
  6. washThe solid was washed with EtOAc
  7. filtrationfiltered

Sources & evidence

ORD record
ord-0d1789c075bf45608a8b5b6270c6d248
Source dataset
uspto-grants-2010_08
Patent number
US07772238B2

Reaction notes

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