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Triphenylphosphine → Triphenyl[(quinolin-2-yl)methyl]phosphanium chloride

HRID 892145
Notes
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Reaction equation

HRID 892145 reaction equation
[Cl:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C.CCOCC>[Cl-:1].[C:26]1([P+:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:2][C:3]2[CH:12]=[CH:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 203942-(Chloromethyl)quinoline

Product 1

HCID 22241267Triphenyl[(quinolin-2-yl)methyl]phosphanium chloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-chloromethyl-quinoline (2.9 g, 20 mmol) in acetonitrile (32 mL) is added triphenylphosphine (4.49 g, 17 mmol). The resulting mixture is warmed to 60° C. and stirred at this temperature for 15 h. This mixture is cooled, diluted with ether, then filtered. The solid is washed with ether, then dried under high vacuum to give the title compound as a solid. 1H NMR (300 MHz, CDCl3) δ 8.20 (d, 1H), 8.06 (d, 1H), 7.95 (m, 6H), 7.42–7.8 (m, 13H), 6.10 (d, 2H).

Workup

  1. temperatureThis mixture is cooled
  2. filtrationfiltered
  3. washThe solid is washed with ether
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-bcd707aada694e4a99c24eac724329cc
Source dataset
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07005440B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes