Lithium hydroxide, monohydrate → 5-Nitroindole-2-carboxylic acid

HRID 221226

반응식

HRID 221226 반응식
O[Li].O.C([O:6][C:7]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][CH:12]=2)=[O:8])C>C1COCC1.CO.O>[N+:18]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:7]([OH:8])=[O:6])=[CH:17]2)([O-:20])=[O:19]

참가 물질

4

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 280312Ethyl 5-nitro-1H-indole-2-carboxylate

생성물 1

HCID 3512915-Nitroindole-2-carboxylic acid

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

반응 조건

온도
25 °C

실험 절차

LiOH.H2O (1.06 g, 46.2 mmol, 2.1 eq.) was added to a suspension of 5-nitro-1H-indole-2-carboxylic acid ethyl ester (II) (5.15 g, 22 mmol, 1 eq.) in THF/MeOH/H2O 1:1:2 (180 ml). The final suspension turned to dark yellow and was stirred at 25° C. After 30 min the solubilization was complete and total conversion was achieved after 6 hours. The reaction mixture was cooled to 0° C. and quenched with HCl 2N until the solution reached pH 5. Organic volatiles were removed under reduced pressure and the white precipitate was filtered and dried to give the compound of formula (III). Yield=4.53 g (quantitative).

후처리

  1. waittotal conversion was achieved after 6 hours
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customquenched with HCl 2N until the solution
  4. customOrganic volatiles were removed under reduced pressure
  5. filtrationthe white precipitate was filtered
  6. customdried

출처 및 근거

ORD 기록
ord-0fc560e3f5c74fd9bd4f1d068875e49a
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207165B2

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