Phosphorus oxychloride → 6,7-Dimethoxy-1-methyl-3,4-dihydroisoquinoline hydrochloride

HRID 35221

Reaction equation

HRID 35221 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)(=O)[CH3:2].P(Cl)(Cl)([Cl:19])=O>C1(C)C=CC=CC=1>[ClH:19].[CH3:16][O:15][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][C:10]=1[O:13][CH3:14])[C:1]([CH3:2])=[N:4][CH2:5][CH2:6]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 80465N-Acetyl-3,4-dimethoxyphenethylamine

Product 1

HCID 123273036,7-Dimethoxy-1-methyl-3,4-dihydroisoquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of N-acetyl-3,4-dimethoxyphenethylamine (112.1 g, 0.502 m) in toluene (600 ml) maintained at 90°-95° was added dropwise phosphorusoxychloride (180.9 g, 112 ml, 1.179 mole) over a period of 1 hour. The mixture was heated to reflux for 2 hr, cooled to ambient temperature, and the solid hydrochloride salt collected by filtration, 170.4 g (wet with toluene). m.p. (after drying) 202°-203°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hr
  3. filtrationthe solid hydrochloride salt collected by filtration, 170.4 g (wet with toluene)
  4. custom(after drying) 202°-203°

Sources & evidence

ORD record
ord-3f124eeca23c4902a25ecfbafa2db0cd
Source dataset
uspto-grants-1988_08
Patent number
US04766131

Linked notes

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