Dimethylformamide → 2,4-Dimethoxyquinoline

HRID 1196554Notes

Reaction equation

HRID 1196554 reaction equation
Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][O-:14].[Na+].CN(C)[CH:18]=[O:19]>>[CH3:18][O:19][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][O:14][C:2]1[CH:11]=[C:10]([O:19][CH3:18])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6075032,4-DichloroquinolineHCID 10942334Sodium Methoxide

Product 2

HCID 1424362,4-DimethoxyquinolineHCID 109653774-Chloro-2-methoxyquinoline

Procedure

2,4-Dichloroquinoline (cf. example 14) (4.4 g), sodium methoxide (5.4 g) and dimethyl formamide (70 ml) were heated together at 70° for 2 hrs. The reaction mixture was partitioned between water and ethyl acetate and worked up in standard fashion. The crude product was purified by column chromatography on silica (10% ether in hexane) to give 2-methoxy-4-chloroquinoline (0.87 g) and 2,4-dimethoxyquinoline (1.8 g). The latter was subjected to aqueous hydrolysis by 6N hydrochloric acid for 3 hrs at reflux temperature to give 2-hydroxy-4-methoxyquinoline. This was converted to 2-chloro-4-methoxyquinoline.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customThe crude product was purified by column chromatography on silica (10% ether in hexane)

Sources & evidence

ORD record
ord-269bae02c7244736b92442218475d5ed
Source dataset
uspto-grants-1992_05
Patent number
US05114940

Reaction notes

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