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

HRID 1986647노트

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HRID 1986647 반응식
[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]>C(O)(=O)C.Cl>[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]

참가 물질

4

반응물 1

HCID 57722418Methyl 7-nitrobenzo[b]thiophene-2-carboxylate

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 313Hydrochloric Acid용매

실험 절차

To a mixture of 7-nitro-benzo[b]thiophene-2-carboxylic acid methyl ester (100 mg) in acetic acid (4 mL) was added a solution of SnC2.2H2O (10 eq) in 1.5 mL of concentrated HCl. The reaction was stirred at room temperature 12 h. The excess acid was partially removed in vacuo, and the reaction mixture was then poured into a flask (250 mL) and was neutralized with saturated NaHCO3 solution at 0° C. The pH was brought up to pH 9 by adding solid NaHCO3. The resulting aqueous mixture was diluted with EtOAc, and the Tin-by product was removed by filtering through a pad of diatomaceous earth. The pad was rinsed with EtOAc and the combined filtrates were partitioned in a separatory funnel. The aqueous layer was extracted with EtOAc two times times. The combined organics were dried over MgSO4, filtered and concentrated to give the desired 7-amino-benzo[b]thiophene-2-carboxylic acid methyl ester (100%).

후처리

  1. customThe excess acid was partially removed in vacuo
  2. additionthe reaction mixture was then poured into a flask (250 mL)
  3. customwas neutralized with saturated NaHCO3 solution at 0° C
  4. additionby adding solid NaHCO3
  5. additionThe resulting aqueous mixture was diluted with EtOAc
  6. customthe Tin-by product was removed
  7. filtrationby filtering through a pad of diatomaceous earth
  8. washThe pad was rinsed with EtOAc
  9. customthe combined filtrates were partitioned in a separatory funnel
  10. extractionThe aqueous layer was extracted with EtOAc two times times
  11. dry with materialThe combined organics were dried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3be63abe472f44f9b1eb7d94f1922fc9
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550461B2

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