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

HRID 361863Notes

Reaction equation

HRID 361863 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-23e55e555ae34bddb975c48e783e192f
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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