Water → HCID 10618283, compound

HRID 1974566Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11](=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=1)[CH:6]=[C:5]2[CH2:22][CH2:23][CH2:24][C:25]([O:27]CC1C=CC=CC=1)=[O:26].O1CCOCC1.O>CO.[Pd]>[NH2:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[C:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[C:5]([CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:6]1)=[O:21]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of benzyl 4-[5-chloro-1-(3-nitrobenzoyl)indol-3-yl]butyrate (1.3 g) in a mixture of methanol (35 ml), 1,4-dioxane (35 ml) and water (5 ml) was added 10% palladium on activated carbon (400 mg), and the mixture was stirred under hydrogen atmosphere (3 atm) at 20° C. for 4 hours. The catalyst was filtered off and the filtrate was evaporated. The residue was chromatographed on silica gel (40 g) eluting with 2% methanol in chloroform to give 4-[1-(3-aminobenzoyl)-5-chloroindol-3-yl]butyric acid (731 mg) as pale yellow crystals.

Workup

filtrationThe catalyst was filtered off
customthe filtrate was evaporated
customThe residue was chromatographed on silica gel (40 g)
washeluting with 2% methanol in chloroform

Sources & evidence

ORD record: ord-3d4c91fe38744679badd3b6cf2b2af15
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05283251

Reaction notes

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