Methanol → 6-(Decanoylamino)-1H-indole-4-carboxylic acid

HRID 1419093Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:13]=[C:12]([NH:14][C:15](=[O:25])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2)=[O:4].CO>O1CCCC1.[OH-].[K+].O>[C:3]([C:5]1[CH:13]=[C:12]([NH:14][C:15](=[O:25])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2)([OH:4])=[O:2]

Participants

Conditions

Temperature: 80 °C

Procedure

Five hundred-fifteen mg of 4-methoxycarbonyl-6-(N-decanoylamino)indole [prepared by the method of Wender et al., PNAS, 83, 4214-4218 (1986)] was dissolved in 60 mL of tetrahydrofuran. This solution was treated with 3 mL of a IN KOH solution in water and also with 5 mL of methanol. The mixture was heated at 80° C. for 32 h. During this period another 2.5 mL of 1N KOH was added in two portions. After cooling the mixture was concentrated in vacuo. The mixture was then diluted with water and acidified with concentrated hydrochloric acid. The mixture was then extracted with methylene chloride. The organic layers were dried over sodium sulfate and concentrated to afford 300 mg of 4-carboxy-6-(N-decanoylamino)indole (60% yield). mp 248°-50° C.

Workup

temperatureAfter cooling the mixture
concentrationwas concentrated in vacuo
additionThe mixture was then diluted with water
extractionThe mixture was then extracted with methylene chloride
dry with materialThe organic layers were dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-be816d5b2b4444bcbc64cd5ecfeb5b8b
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05886017

Reaction notes

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