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

HRID 1703210Notes

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 temperature was maintained at 55° C. for an additional one-half hour. The reaction was then cooled to room temperature 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 =R0 =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 temperature
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-1608349c283f484aacf7a80b4214a08b
Source dataset: uspto-grants-1982_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04351768

Reaction notes

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