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

HRID 361863노트

반응식

HRID 361863 반응식
[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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium Hydroxide2회HCID 4715068methyl 6-(benzyloxy)-1H-indole-2-carboxylate

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-23e55e555ae34bddb975c48e783e192f
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866589

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