Acetone → 1-(3-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinolin-4-yl)-but-1-en-3-one

HRID 235596Notes

Reaction equation

HRID 235596 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH3:14])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[CH:12]=O.[OH-].[Na+].O.[CH3:18][C:19]([CH3:21])=[O:20]>>[Cl:1][C:2]1[N:3]=[C:4]([CH3:14])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[CH:12]=[CH:18][C:19](=[O:20])[CH3:21]

Participants

5

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 139353363-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinoline-4-carboxaldehyde

Product 1

HCID 537568801-(3-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinolin-4-yl)-but-1-en-3-one

Procedure

3-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinoline-4-carboxaldehyde (4.0 g) was stirred with a few drops of a 2% aqueous sodium hydroxide solution in aqueous acetone (1:2 v/v; 20 ml) at room temperature for 4 hr. The mixture was poured into water which was then extracted with diethyl ether. The residue obtained after evaporation of the dried (MgSO4) organic extract was purified by column chromatography over silica with dichloromethane elution to give 1-(3-chloro-1-methyl-5,6,7,8-tetrahydroisoquinolin-4-yl)-but-1-en-3-one as white crystals, mp 90° C.

Workup

  1. extractionwas then extracted with diethyl ether
  2. customThe residue obtained
  3. customafter evaporation of the
  4. dry with materialdried (MgSO4)
  5. extractionorganic extract
  6. customwas purified by column chromatography over silica with dichloromethane elution

Sources & evidence

ORD record
ord-640c9f60e3554f72b839d87c359fa91d
Source dataset
uspto-grants-1987_02
Patent number
US04640708

Reaction notes

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