Dimethylformamide → N-phenyl-2-chloroquinolinium chloride

HRID 1648204Notes

Reaction equation

HRID 1648204 reaction equation
[C:1]1([N:7](C2C=CC=CC=2)[C:8](=O)[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:19])=O.CN(C=O)C.S([C:31]1[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=1)([O-])(=O)=O.C[N+]1C2C=CC=CC=2SC=1C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl-:19].[C:1]1([N+:7]2[C:36]3[C:34](=[CH:33][CH:32]=[CH:31][CH:37]=3)[CH:35]=[CH:9][C:8]=2[Cl:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10615N,N-DiphenylacetamideHCID 24813Phosphorus oxychlorideHCID 102307Benzothiazolium, 2,3-dimethyl-, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 19918906N-phenyl-2-chloroquinolinium chloride

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The intermediate N-phenyl-2-chloroquinolinium chloride is prepared according to the literature method (Marson, TETRAHEDRON, 48, 3659 (1992)). Thus 1.06 g (5 mmoles) of N, N-diphenyl acetamide is heated with 1.69 g (11 mmoles) of phosphorous oxychloride and 0.44 g (6 mmoles) of DMF at 120° C. for 2 hours. The reaction mixture is cooled to room temperature and 15 mL of methylene chloride is added to dissolve the residue. To the solution is added 1.68 g (5 mmoles) of N,2-dimethylbenzothiazolium tosylate and 1.46 g (12 mmoles) of 4-dimethylaminopyridine, and the reaction is stirred overnight (Elderfield, supra). The crude product is first purified on a silica gel column eluting with 2:2:1 ethyl acetate/chloroform/methanol and then metathesized to the iodide salt and recrystallized from methanol to obtain the pure product.

Workup

  1. dissolutionto dissolve the residue
  2. customThe crude product is first purified on a silica gel column
  3. washeluting with 2:2:1 ethyl acetate/chloroform/methanol
  4. customrecrystallized from methanol
  5. customto obtain the pure product

Sources & evidence

ORD record
ord-4262062deba84b3989476dfe0c6af86d
Source dataset
uspto-grants-1995_07
Patent number
US05436134

Reaction notes

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