Hydrochloric Acid → 2-Oxo-3-[5-(3-pyrrolidin-1-yl-propyl)-1H-indol-2-ylmethylene]-2,3-dihydro-1H-indole-5-carboxylic acid

HRID 1790932Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)([OH:3])=[O:2].[CH2:14]([N:16]([CH2:31][CH3:32])[CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([CH:29]=O)=[CH:23]2)[CH3:15].N1CCCCC1.Cl>C(O)C>[O:13]=[C:8]1[C:7](=[CH:29][C:24]2[NH:25][C:26]3[C:22]([CH:23]=2)=[CH:21][C:20]([CH2:19][CH2:18][CH2:17][N:16]2[CH2:31][CH2:32][CH2:15][CH2:14]2)=[CH:28][CH:27]=3)[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([C:1]([OH:3])=[O:2])[CH:5]=2)[NH:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-carboxy-2-oxindole (35 mg, 0.2 mmol), 5-(3-diethylamino-propyl)-1H-indole-2-carbaldehyde (51 mg, 0.2 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 80° C. for 6 hours. The reaction was acidified with 1 N HCl and the precipitate was collected by vacuum filtration, washed with 1 N HCl, water and ethanol, dried to give the title compound.

Workup

filtrationthe precipitate was collected by vacuum filtration
washwashed with 1 N HCl, water and ethanol
customdried

Sources & evidence

ORD record: ord-0f579a24fb5e4ee5a5f70e5cfc3fa5ac
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071332B2

Reaction notes

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