Sodium Hydroxide → 2-[(1-Ethyl-2-methyl3-indolyl)carbonyl]-5-aminobenzoic acid

HRID 1449087Notes

Reaction equation

[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([C:14]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][C:15]=2[C:16]([OH:18])=[O:17])=[O:13])=[C:4]1[CH3:26])[CH3:2].[OH-].[Na+]>Cl>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([C:14]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:15]=2[C:16]([OH:18])=[O:17])=[O:13])=[C:4]1[CH3:26])[CH3:2]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 7.04 g (0.02 mole) of 2-[(1-ethyl-2-methyl-3-indolyl)carbonyl]-5-nitrobenzoic acid, prepared as described in part A of this example, in 70 ml of concentrated hydrochloric acid, there was added 13.5 g (0.06 mole) of stannous chloride dihydrate at such a rate as to allow the reaction to exotherm to 55° C. The temprature was maintained at 55° C. for an additional one-half hour. The reaction was then cooled to room temprature and the pH adjusted to six by the addition of 10 percent aqueous sodium hydroxide solution. The red precipitate thus formed was filtered off and extracted into acetone. The acetone solution was evaporated and the paste-like residue was slurried in diethylether and then the solid was collected by filtration to obtain 3.5 g of 2-[(1-ethyl-2-methyl-3-indolyl)-carbonyl]-5-aminobenzoic acid (Formula VIII: R3 =R2 =R°=Y1 =H; R1 =NH2 ; R5 =CH3 ; R6 =CH2CH3), a red solid which melted at 187°-189° C.

Workup

customthe reaction
customto exotherm to 55° C
temperatureThe reaction was then cooled to room temprature
customThe red precipitate thus formed
filtrationwas filtered off
extractionextracted into acetone
customThe acetone solution was evaporated
filtrationthe solid was collected by filtration

Sources & evidence

ORD record: ord-8c9fc533165242f482b94dbf62eed45f
Source dataset: uspto-grants-1980_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04189171

Reaction notes

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