Dimethylamine → 3-Butyryl-4-(2-methylphenylamino)-8-(1-hydroxy-2-dimethylaminoethyl)quinoline

HRID 1090665Notes

Reaction equation

HRID 1090665 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:24]1[CH2:26][O:25]1)(=[O:5])[CH2:2][CH2:3][CH3:4].[CH3:27][NH:28][CH3:29]>>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:24]([OH:25])[CH2:26][N:28]([CH3:29])[CH3:27])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 99749123-Butyryl-4-(2-methylphenylamino)-8oxiranylquinoline

Product 1

HCID 100690393-Butyryl-4-(2-methylphenylamino)-8-(1-hydroxy-2-dimethylaminoethyl)quinolineYield 28%

Procedure

A mixture of 3-butyryl-4-(2-methylphenylamino)-8oxiranylquinoline (1.0 g, 2.89 mmol) and 33% w/w dimethylamine in methylated spirits (10 ml) was heated at 95° for 2 hours in a pressure vessel. After cooling and evaporation of the solvent, the residue was purified by flash chromatography (silica gel, methanolic ammonia/dichloromethane) and crystallistion from aqueous ethanol to give 3-butyryl-4-(2-methylphenylamino)-8-(1-hydroxy-2-dimethylaminoethyl)quinoline (0.32 g, 28%), m.p. 95°-96°.

Workup

  1. temperaturewas heated at 95° for 2 hours in a pressure vessel
  2. temperatureAfter cooling
  3. customevaporation of the solvent
  4. customthe residue was purified by flash chromatography (silica gel, methanolic ammonia/dichloromethane) and crystallistion from aqueous ethanol

Sources & evidence

ORD record
ord-a220d000b1444199b0bf621bf0f73e5f
Source dataset
uspto-grants-1992_01
Patent number
US05082841

Reaction notes

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