Hydrochloric Acid → 1-[2-(4-Chloro-phenyl)-ethyl]-1H-indole-2-carboxylic acid

HRID 1071674Notes

Reaction equation

HRID 1071674 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1.O>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][CH2:15][N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:14]=[C:6]2[C:4]([OH:5])=[O:3])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 688562801-[2-(4-Chloro-phenyl)-ethyl]-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 223943811-[2-(4-Chloro-phenyl)-ethyl]-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

480 mg (1.5 mmol) of 1-[2-(4-Chloro-phenyl)-ethyl]-1H-indole-2-carboxylic acid ethyl ester was dissolved in 5 ml of dioxan and 5 ml of 2N aqueous sodium hydroxide was added. The reaction was heated to 60° C. for 2 h, then was cooled to 0° C. The solution was diluted with 10 ml of water and the pH of the solution was adjusted to between 2 and 3 by the addition of concentrated aqueous HCl, whereupon the product precipitates. The product was filtered off and dried under reduced pressure. Yield: 390 mg MS (Cl+): m/e=300, chloro pattern.

Workup

  1. temperaturewas cooled to 0° C
  2. customprecipitates
  3. filtrationThe product was filtered off
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-b61c2b53009e4c918e7f953f6e8c9eee
Source dataset
uspto-grants-2005_06
Patent number
US06906084B2

Reaction notes

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