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

HRID 49080Notes

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 1N HCl and the precipitate was collected by vacuum filtration, washed with 1N HCl, water and ethanol, dried to give the title compound.

Workup

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

Sources & evidence

ORD record: ord-425992ee689045699c957ea3577f4672
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706709B2

Reaction notes

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