Hydrochloric Acid → 6-(benzyloxy)-1H-indole-2-carboxylic acid

HRID 361863ノート

反応式

HRID 361863 の反応式
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:18]([O:20]C)=[O:19])[NH:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[K+].Cl>O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:18]([OH:20])=[O:19])[NH:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium Hydroxide2 回HCID 4715068methyl 6-(benzyloxy)-1H-indole-2-carboxylate

生成物 1

HCID 51149926-(benzyloxy)-1H-indole-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

Methyl 6-benzyloxyindole-2-carboxylate (EXAMPLE 247, 3.77 g) is dissolved in 33.5 ml of dioxane and 3.35 ml of water is added. Then solid potassium hydroxide (0.9 g) is added and the reaction is heated to 50° for 6 hr. Then a further 0.9 g of potassium hydroxide is added and the reaction is stirred at 20°-25° for 72 hr and heated at 50° a further 4 hr. Then it is cooled to 20°-25° and acidified to pH 4-5 with 2N hydrochloric acid. The reaction is extracted with methanol/chloroform (10/90, 3 times) and the extracts are dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to provide the title compound.

後処理

  1. temperaturethe reaction is heated to 50° for 6 hr
  2. temperatureheated at 50° a further 4 hr
  3. temperatureThen it is cooled to 20°-25°
  4. extractionThe reaction is extracted with methanol/chloroform (10/90, 3 times)
  5. dry with materialthe extracts are dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-23e55e555ae34bddb975c48e783e192f
出典データセット
uspto-grants-1999_02
特許番号
US05866589

反応ノート

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