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Sodium hydride → 1H-Indole-7-propanenitrile, 1-[[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]methyl]-, (E)-

HRID 1198541
Notes
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Reaction equation

HRID 1198541 reaction equation
[C:1]([CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][CH:11]=[CH:10]2)#[N:2].[H-].[Na+].[Cl:16][C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[CH:22][C:23](/[CH:27]=[CH:28]/[C:29]3[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=3)[CH2:32]Cl)=[N:24]2)=[CH:19][CH:18]=1.[Cl-].[NH4+]>CN(C)C=O>[C:1]([CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[N:12]([CH2:32][C:31]1[CH:34]=[CH:35][CH:36]=[C:29](/[CH:28]=[CH:27]/[C:23]3[CH:22]=[CH:21][C:20]4[C:25](=[CH:26][C:17]([Cl:16])=[CH:18][CH:19]=4)[N:24]=3)[CH:30]=1)[CH:11]=[CH:10]2)#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 19369489trans-3-[2-(7-Chloroquinolin-2-yl)ethenyl]benzyl chlorideHCID 199591053-(1H-Indol-7-YL)propanenitrile

Product 1

HCID 191026011H-Indole-7-propanenitrile, 1-[[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]methyl]-, (E)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 7-(2-cyanoethyl)indole (Example 14a) (4.42 g, 26 mmol) in dimethylformamide (30 ml) was added dropwise to a stirred suspension of sodium hydride (1.3 g, 60% dispersion, 32.5 mmol, washed with hexane under nitrogen) in dimethylformamide (30 ml) at 10°-15° C. The mixture was stirred for 15 minutes at ca 15° C. then a suspension of 3-[2(E)-(7-chloroquinolin-2-yl)ethenyl] benzyl chloride (Example 14b) (10.2 g, 32.5 mmol) in dimethylformamide (60 ml) was added rapidly. The dark mixture was stirred for 5 hours at room temperature, poured onto saturated ammonium chloride solution and extracted with dichloromethane. The extract was dried and evaporated under high vacuum and the residue in dichloromethane (30 ml) was applied to a silica column and eluted with ethyl acetate-hexane (1:2). The product was recrystallised from ethyl acetate-hexane, m.p. 151° C.

Workup

  1. additionwas added rapidly
  2. stirringThe dark mixture was stirred for 5 hours at room temperature
  3. extractionextracted with dichloromethane
  4. customThe extract was dried
  5. customevaporated under high vacuum
  6. washeluted with ethyl acetate-hexane (1:2)
  7. customThe product was recrystallised from ethyl acetate-hexane, m.p. 151° C.

Sources & evidence

ORD record
ord-f6249be6704b456aaa971ddb5179a7e7
Source dataset
uspto-grants-1994_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05281593

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes