Phosphorus oxychloride → 3,4-Dihydro-7-methoxy-1-phenylisoquinoline

HRID 383987Notes

Reaction equation

HRID 383987 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][CH2:8][NH:9][C:10](=O)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.O=P(Cl)(Cl)Cl>CC#N>[CH3:1][O:2][C:3]1[CH:19]=[C:18]2[C:6]([CH2:7][CH2:8][N:9]=[C:10]2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 3083797Benzamide, N-(2-(4-methoxyphenyl)ethyl)-

Product 1

HCID 102635563,4-Dihydro-7-methoxy-1-phenylisoquinolineYield 661.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4.0 g (15.7 mmol) of N-(4-methoxyphenethyl)benzamide and 21.1 ml (227.0 mmol) of POCl3 in MeCN (120 ml) was refluxed for 16 h. The mixture was then concentrated to small volume under vacuum, taken up with MeOH and concentrated to small volume under vacuum again. This step was repeated three times. 24.65 g of the crude product 7-methoxy-1-phenyl-3,4-dihydroisoquinoline were obtained as the residue, which was reacted further with no additional purification.

Workup

  1. temperaturewas refluxed for 16 h
  2. concentrationThe mixture was then concentrated to small volume under vacuum
  3. concentrationconcentrated to small volume under vacuum again

Sources & evidence

ORD record
ord-db26f112cfc44e9d9acf187c585326b7
Source dataset
uspto-grants-2013_02
Patent number
US08367700B2

Reaction notes

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