Dimethylformamide → Quinoline, 4-chloro-6,8-dimethoxy-

HRID 1720284Notes

Reaction equation

HRID 1720284 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:13][CH3:14])[CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2O.P(Cl)(Cl)([Cl:18])=O.CN(C)C=O>O>[Cl:18][C:6]1[C:5]2[C:10](=[C:11]([O:13][CH3:14])[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178493408HCID 178493408, compound

Product 1

HCID 22417920Quinoline, 4-chloro-6,8-dimethoxy-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6.5 g (31.6 mmol) of 6,8-dimethoxyquinolin-4-ol, 29 mL (316 mmol) of phosphorous oxychloride and 2.6 mL of N,N-dimethylformamide was stirred at room temperature for seven hours. The reaction solution was poured into a stirred mixture of ice and water. The aqueous mixture was washed three times with 300 mL portions of ethyl acetate, and then adjusted to pH 6 by the addition of solid sodium carbonate. 4-Chloro-6,8-dimethoxyquinoline was thus obtained as a colorless solid: yield 5.73 g (81%). The product was recrystallized from hot water for analysis: m.p. 115°-116° C.

Workup

  1. washThe aqueous mixture was washed three times with 300 mL portions of ethyl acetate
  2. additionadjusted to pH 6 by the addition of solid sodium carbonate

Sources & evidence

ORD record
ord-6a501d1364a04adebb3c11f9f5fca3cb
Source dataset
uspto-grants-1996_04
Patent number
US05506235

Reaction notes

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