Hydrochloric Acid → Allyl 2-(indol-6-yl)acetate

HRID 1417472Notes

Reaction equation

HRID 1417472 reaction equation
Cl.C(N=C=N[CH2:7][CH2:8][CH2:9]N(C)C)C.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][C:23]([OH:25])=[O:24])[CH:20]=2)[CH:15]=[CH:14]1.C(O)C=C.Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][C:23]([O:25][CH2:9][CH:8]=[CH2:7])=[O:24])[CH:20]=2)[CH:15]=[CH:14]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7858Allyl AlcoholHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 148825031H-Indole-6-acetic acid

Product 1

HCID 53949354Allyl 2-(indol-6-yl)acetateYield 86.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

750 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added to a solution of 450 mg of 2-(indol-6-yl)acetic acid [synthesized according to the procedures described in Chem. Pharm. Bull., 20, 2163 (1972)], 0.27 ml of allyl alcohol and 480 mg of 4-dimethylaminopyridine in 20 ml of methylene chloride, at room temperature, and the resulting mixture was stirred overnight. After completion of the reaction, the reaction mixture was acidified by the addition of a 3% aqueous solution of hydrochloric acid, followed by extraction with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate, and then the solvent was removed by evaporation under reduced pressure. The resulting residue was subjected to column chromatography using 10 g of silica gel with a 4:1 v/v mixture of hexane and ethyl acetate as the eluent, to yield 480 mg of the title compound as an oil.

Workup

  1. customsynthesized
  2. customAfter completion of the reaction
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed by evaporation under reduced pressure
  7. additionwith a 4:1 v/v mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-7e5b312dff3446ea9223d176a57efab3
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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