Stannous Chloride → Ethyl 6-amino-1H-indole-4-carboxylate

HRID 401273노트

반응식

HRID 401273 반응식
[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[C:7]([N+]([O-])=O)[C:6]=1[CH:17]=[CH:18][N:19](C)C)[CH3:2].Cl[Sn]Cl>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[C:6]2[CH:17]=[CH:18][NH:19][C:7]=2[CH:8]=[C:9]([NH2:11])[CH:10]=1)=[O:22])[CH3:2]

참가 물질

4

반응물 2

HCID 24479Stannous ChlorideHCID 76548813HCID 76548813, 화합물

생성물 1

HCID 53435938Ethyl 6-amino-1H-indole-4-carboxylate수율 40%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-(2-dimethylamino-vinyl)-3,5-dinitro-benzoic acid ethyl ester (11.3 g, 0.037 mol) and SnCl2 (83 g. 0.37 mol) in ethanol was heated at reflux for 4 h. The mixture was concentrated to dryness and the residue was poured into water and basified with sat. Na2CO3 solution to pH 8. The precipitate was filtered off and the filtrate was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with water (2×100 mL) and brine (150 mL), dried over Na2SO4 and concentrated to dryness. The residue was purified by column chromatography on silica gel to give 6-amino-1H-indole-4-carboxylic acid ethyl ester (B-18) (3 g, 40%). 1H NMR (DMSO-d6) δ 10.76 (br s, 1H), 7.11-7.14 (m, 2H), 6.81-6.82 (m, 1H), 6.67-6.68 (m, 1H), 4.94 (br s, 2H), 4.32-4.25 (q, J=7.2 Hz, 2H), 1.35-1.31 (t, J=7.2, 3 H). ESI-MS 205.0 m/z (MH+).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. concentrationThe mixture was concentrated to dryness
  4. additionthe residue was poured into water and basified with sat. Na2CO3 solution to pH 8
  5. filtrationThe precipitate was filtered off
  6. extractionthe filtrate was extracted with ethyl acetate (3×100 mL)
  7. washThe combined extracts were washed with water (2×100 mL) and brine (150 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated to dryness
  10. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-cadaadd4fc7a498dac18a8d6d37a65cc
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741925B2

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