Sodium Carbonate → 4-(2,3-dihydro-1H-indol-6-ylamino)-6,7-diethoxy-quinoline-3-carbonitrile

HRID 1595752Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].Cl.Cl.[NH2:22][C:23]1[CH:31]=[C:30]2[C:26]([CH2:27][CH2:28][NH:29]2)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[NH:29]1[C:30]2[C:26](=[CH:25][CH:24]=[C:23]([NH:22][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=4)[N:5]=[CH:4][C:3]=3[C:18]#[N:19])[CH:31]=2)[CH2:27][CH2:28]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 400 mg (1.44 mM) of 4-chloro-6,7-diethoxy-quinoline-3-carbonitrile and 258 mg (1.88 mM) of 6-Aminoindoline dihydrochloride salt in 10 ml of ethanol was refluxed for 3 hours. To the warm solution was added 1 ml of 1M sodium carbonate and the sample was heated for 5 minutes at 100° C., then poured into 300 ml of ice water. The solid was collected, washed with water followed by ether and dried under vacuum at 80° C. The solid was dissolved in 50/50 methanol/chloroform and dried onto silica gel and purified by chromatography using a gradient of 20% to 50% acetone in hexane to yield 496 mg of the title compound as a tan solid: mass spectrum (electrospray, m/e): M+H 375.1, mp=121-124° C.

Workup

customThe solid was collected
washwashed with water
customdried under vacuum at 80° C
dissolutionThe solid was dissolved in 50/50 methanol/chloroform
customdried onto silica gel
custompurified by chromatography

Sources & evidence

ORD record: ord-f3312fe737f84c328ee1d344ea7fa217
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288082B1

Reaction notes

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