Hydrochloric Acid → (4-acetylamino-2-methyl-1H-indol-1-yl)acetic acid

HRID 505933Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([CH3:20])[N:9]2[CH2:14][C:15]([O:17]CC)=[O:16])(=[O:3])[CH3:2].[OH-].[Na+].Cl>C(O)C>[C:1]([NH:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([CH3:20])[N:9]2[CH2:14][C:15]([OH:17])=[O:16])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

(4-Acetylamino-2-methyl-1H-indol-1-yl)-acetic acid, ethyl ester (2.0 g, 7.3 mmol) was slurried in ethanol (10 ml) at ambient temperature. Aqueous sodium hydroxide (1 M, 10 ml, 10 mmol) was added and the mixture heated to 50° C. The solution obtained at was then allowed to cool back to ambient temperature and aqueous hydrochloric acid (1 M, 11 ml, 11 mmol) added. The resulting solid was collected by filtration, washed with water (2×10 ml) then dried in a vacuum oven at 45° C. overnight to provide (4-acetylamino-2-methyl-1H-indol-1-yl)acetic acid as an off-white solid, 1.66 g (92%).

Workup

customThe solution obtained
temperatureto cool back to ambient temperature
filtrationThe resulting solid was collected by filtration
washwashed with water (2×10 ml)
customthen dried in a vacuum oven at 45° C. overnight

Sources & evidence

ORD record: ord-de8e90dd223f4afab4ab07b5f3c96946
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781598B2

Reaction notes

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