Hydrochloric Acid → Methyl 5-amino-1-benzothiophene-2-carboxylate

HRID 252788노트

반응식

HRID 252788 반응식
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([N+:14]([O-])=O)=[CH:13][C:7]=2[CH:6]=1)=[O:4].Cl>CO.[Fe]>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([NH2:14])=[CH:13][C:7]=2[CH:6]=1)=[O:4]

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 1489057Methyl 5-nitro-1-benzothiophene-2-carboxylate

생성물 1

HCID 2824064Methyl 5-amino-1-benzothiophene-2-carboxylate

시약·촉매·용매 2

HCID 23925Iron촉매HCID 887Methanol용매

실험 절차

A suspension of 584 (3.52 g, 14.8 mmol) in methanol (100 ml) was treated with Fe powder (6.63 g, 118.7 mmol). The resulting suspension was heated to reflux, and 12M HCl (8.5 ml) was slowly added over 15 min. The resulting green dark suspension was refluxed for an additional 3 h, then cooled and concentrated. The residue was taken up in EtOAc and washed with saturated aqueous NaHCO3, then brine, dried over MgSO4, filtered and concentrated to afford (2.57 g, 84%). 1H NMR: (DMSO) δ (ppm): 7.92 (s, 1H), 7.65 (d, J=8.8 Hz, 1H), 7.05 (d, J=1.5 Hz, 1H), 6.88 (dd, J=1.8, 8.4 Hz, 1H), 5.27 (s, 2H), 3.85 (s, 3H). LRMS: 207.0 (Calc.); 208.1 (found).

후처리

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux
  3. temperatureThe resulting green dark suspension was refluxed for an additional 3 h
  4. temperaturecooled
  5. concentrationconcentrated
  6. washwashed with saturated aqueous NaHCO3
  7. dry with materialbrine, dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford (2.57 g, 84%)

출처 및 근거

ORD 기록
ord-d0d998f38d3444b4b6bad1640d68c41d
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868204B2

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