Hydrochloric Acid → 1-(4-chlorobenzyl)-7-methyl-1H-indole-2-carboxylic acid

HRID 83680Notes

Reaction equation

[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[CH3:16])[CH:9]=[C:8]2[C:17]([O:19]CC)=[O:18])=[CH:4][CH:3]=1.[OH-].[K+].Cl>CCO>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[CH3:16])[CH:9]=[C:8]2[C:17]([OH:19])=[O:18])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

ethyl 1-(4-chlorobenzyl)-7-methyl-1H-indole-2-carboxylate (212 mg, 0.647 mmol) was dissolved in EtOH (10 mL) and 10% aq. KOH (10 mL) was added. The reaction stirred for 4 h at 70° C., after which time as much solvent was stripped off as possible. The mostly aqueous mixture was cooled in an ice bath and acidified with concentrate HCl to obtain a precipitate that was collected over a filter and washed with 1M HCl and water. The title compound was not purified or characterized further. (Yield: 182 mg, 0.607 mmol, 94%).

Workup

temperatureThe mostly aqueous mixture was cooled in an ice bath
customto obtain a precipitate that
customwas collected over
filtrationa filter
washwashed with 1M HCl and water
customThe title compound was not purified

Sources & evidence

ORD record: ord-f4d921ab8ce6418694df645a48989564
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846684B2

Reaction notes

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