Sodium Hydroxide → 1-(5-tert-butyl-2-methoxybenzyl)-5-chloro-1H-indole-2-carboxylic acid

HRID 2242353Notes

Reaction equation

[OH-].[Na+].C([O:5][C:6]([C:8]1[N:9]([CH2:18][C:19]2[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=[CH:21][C:20]=2[O:29][CH3:30])[C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([Cl:17])=[CH:12][CH:11]=2)=[O:7])C>C(O)C>[C:25]([C:23]1[CH:22]=[CH:21][C:20]([O:29][CH3:30])=[C:19]([CH:24]=1)[CH2:18][N:9]1[C:10]2[C:15](=[CH:14][C:13]([Cl:17])=[CH:12][CH:11]=2)[CH:16]=[C:8]1[C:6]([OH:7])=[O:5])([CH3:28])([CH3:26])[CH3:27]

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of 4M aqueous sodium hydroxide (1.10 ml) was added to a solution of 1-(5-tert-butyl-2-methoxybenzyl)-5-chloro-1H-indole-2-carboxylic acid ethyl ester (1.13 g, 2.82 mmol) in ethanol (15 ml) and the reaction heated at 45° C. for 3 h. After concentrating the mixture to 5.0 ml, a solution of 2M aqueous HCl (2.0 ml) was added to precipitate the product as a pale solid which was filtered, washed with water (3×30 ml) and dried under vacuum, affording 1-(5-tert-butyl-2-methoxybenzyl)-5-chloro-1H-indole-2-carboxylic acid (1.03 g, 2.77 mmol, 98%).

Workup

concentrationAfter concentrating the mixture to 5.0 ml
additiona solution of 2M aqueous HCl (2.0 ml) was added
customto precipitate the product as a pale solid which
filtrationwas filtered
washwashed with water (3×30 ml)
customdried under vacuum

Sources & evidence

ORD record: ord-06bee50e9d2b4447892cf809a41ba2a4
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07671080B2

Reaction notes

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