Potassium Hydroxide → HCID 19102579, compound

HRID 1198566Notes

Reaction equation

[OH-].[K+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=2)[CH:5]=[CH:4]1.Cl.[C:15]1([CH:21](Cl)[C:22]2[CH:27]=[CH:26][CH:25]=[C:24](/[CH:28]=[CH:29]/[C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=3)[CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CS(C)=O>[C:15]1([CH:21]([N:3]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=3)[CH:5]=[CH:4]2)[C:22]2[CH:27]=[CH:26][CH:25]=[C:24](/[CH:28]=[CH:29]/[C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=3)[CH:23]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Powdered potassium hydroxide (0.50 g, 8.93 mmol) was added to a stirred solution of indole-6-carboxaldehyde (Example 29a) (0.54 g, 3.70 mmol) in dimethyl-sulphoxide (10 ml). The solution was stirred under nitrogen for 10 minutes then solid a-phenyl-3-[2(E)-(quinolin-2-yl)ethenyl]benzyl chloride hydrochloride (Example 16a) (1.75 g, 4.46 mmol) was added and then stirred mixture was heated at 60° C. for 4 hours. The mixture was poured onto ammonium chloride solution and extracted with dichloromethane and the extract was dried and evaporated. The residue was chromatographed on silica in ethyl acetatehexane (1:3) to give a gummy solid which was recrystallised from ether-hexane, m.p. 75° C.

Workup

stirringstirred mixture
additionThe mixture was poured onto ammonium chloride solution
extractionextracted with dichloromethane
customthe extract was dried
customevaporated
customThe residue was chromatographed on silica in ethyl acetatehexane (1:3)
customto give a gummy solid which
customwas recrystallised from ether-hexane, m.p. 75° C.

Sources & evidence

ORD record: ord-a8fc2d40a1f14b0aa6b56e6388129523
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05281593

Reaction notes

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