Sodium Hydroxide → 6-Methyl-7-methoxy-1-[2-(4-chlorophenyl)ethyl]-3,4-dihydroisoquinoline

HRID 893321Notes

Reaction equation

HRID 893321 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][NH:12][C:13](=O)[CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>O.C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[O:8][CH3:9])[C:13]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)=[N:12][CH2:11][CH2:10]2

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 24813Phosphorus oxychlorideHCID 19892235N-[2-(3-methyl-4-methoxyphenyl)ethyl]-3-(4-chlorophenyl)propionamide

Product 1

HCID 197396936-Methyl-7-methoxy-1-[2-(4-chlorophenyl)ethyl]-3,4-dihydroisoquinolineYield 52.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

Heat a mixture of the amide from step A (10.0 g), phosphorous pentoxide (25 g), phosphorous oxychloride (15 mL) and xylene (250 mL) at reflux for 2 h. Cool the reaction mixture, slowly add water (500 mL), basify using NaOH and extract with benzene. Concentrate the benzene extract to a residue and triturate with diethyl ether to give 6-methyl-7-methoxy-1-[2-(4-chlorophenyl)ethyl]-3,4-dihydroisoquinoline (4.95 g), mp=122°-124° C.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 2 h
  3. extractionextract with benzene
  4. concentrationConcentrate the benzene
  5. extractionextract to a residue
  6. customtriturate with diethyl ether

Sources & evidence

ORD record
ord-33fd2248f5164c60acda88d87f0ff315
Source dataset
uspto-grants-1992_06
Patent number
US05124337

Reaction notes

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