Indole-2-carboxaldehyde → 3-(1H-indol-2-ylmethylene)-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid

HRID 1840491ノート

反応式

HRID 1840491 の反応式
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)([OH:3])=[O:2].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]1[CH:23]=O>N1CCCCC1.C(O)C>[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]1[CH:23]=[C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([C:1]([OH:3])=[O:2])[CH:5]=2)[NH:9][C:8]1=[O:13]

参加物

5

反応物 2

HCID 96389Indole-2-carboxaldehydeHCID 27733182-Oxindole-5-carboxylic acid

生成物 1

HCID 540903703-(1H-indol-2-ylmethylene)-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid収率 40%

試薬・触媒・溶媒 2

HCID 8082Piperidine触媒HCID 702Ethanol溶媒

反応条件

温度
95 °C

実験手順

A mixture of 5-carboxy-2-oxindole (88.5 mg) (prepared as described in Compound IN-05), indole-2-carbaldehyde (87 mg) (prepared according to Synthetic Communications, 1993, 23, 3109) and piperidine (1 drop) in ethanol (3 mL) was heated in a sealed tube at 95° C. for 4 hours. The mixture was cooled to room temperature. The solid was filtered and acidified with 2N hydrochloric acid. The resulting darker solid was collected by vacuum filtration, washed with cold ethanol and dried in vacuum oven for overnight to give 60 mg (40% yield) of 3-(1H-indol-2-ylmethylene)-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid as a mustard-colored solid.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe solid was filtered
  3. filtrationThe resulting darker solid was collected by vacuum filtration
  4. washwashed with cold ethanol
  5. customdried in vacuum oven for overnight

出典と根拠

ORDレコード
ord-c97db97c0d9b49a784ee8ca5880e5230
出典データセット
uspto-grants-2004_01
特許番号
US06680335B2

反応ノート

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