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

HRID 221226

反応式

HRID 221226 の反応式
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]

参加物

4

反応物 2

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

生成物 1

HCID 3512915-Nitroindole-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 21892291Methanol tetrahydrofuran water溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0fc560e3f5c74fd9bd4f1d068875e49a
出典データセット
uspto-grants-2012_06
特許番号
US08207165B2

関連ノート

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