Sodium Hydroxide → HCID 19900496, compound

HRID 1029437Notes

Reaction equation

HRID 1029437 reaction equation
[ClH:1].O[CH2:3][C:4]1[CH:13]=[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[C:11]2[C:6](=[C:7]([O:23][CH3:24])[CH:8]=[CH:9][CH:10]=2)[N:5]=1.S(Cl)([Cl:27])=O.[OH-].[Na+]>CN(C=O)C>[ClH:27].[Cl:1][CH2:3][C:4]1[CH:13]=[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[C:11]2[C:6](=[C:7]([O:23][CH3:24])[CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 19900503HCID 19900503, compound

Product 1

HCID 19900496HCID 19900496, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 2 5 g (=7.2 mmol) of 2-hydroxymethyl-8-methoxy-4-(2-methylbenzylamino)quinoline hydrochloride, 5.3 ml of thionyl chloride and 2 drops of DMF was stirred at room temperature for 90 minutes. The mixture was poured onto ice, made alkaline with 1 N NaOH and extracted with ethyl acetate. The crude product after the organic phase had been dried with Na2SO4 and the solvent had been stripped off was converted into the hydrochloride with methanolic hydrochloric acid. 2.48 g of 2-chloromethyl-8-methoxy-4-(2-methylbenzylamino)quinoline hydrochloride were obtained.

Workup

  1. additionThe mixture was poured onto ice
  2. extractionextracted with ethyl acetate
  3. dry with materialThe crude product after the organic phase had been dried with Na2SO4

Sources & evidence

ORD record
ord-4b157f5fd1f74f57b6867a0c4d465c8b
Source dataset
uspto-grants-1992_04
Patent number
US05102892

Reaction notes

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