Phosphorus oxychloride → 1-(1-chloro-6-methoxy-4-phenylisoquinolin-3-yl)-N,N-dimethylmethanamine

HRID 639875Notes

Reaction equation

HRID 639875 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[NH:6][C:7](=O)[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([O:21][CH3:22])=[CH:10][CH:9]=2)[CH3:3].O=P(Cl)(Cl)[Cl:26]>>[Cl:26][C:7]1[C:8]2[C:13](=[CH:12][C:11]([O:21][CH3:22])=[CH:10][CH:9]=2)[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:5]([CH2:4][N:2]([CH3:3])[CH3:1])[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 685191143-[(dimethylamino)methyl]-6-methoxy-4-phenylisoquinolin-1(2H)-one

Product 1

HCID 117389161-(1-chloro-6-methoxy-4-phenylisoquinolin-3-yl)-N,N-dimethylmethanamine

Procedure

3-[(dimethylamino)methyl]-6-methoxy-4-phenylisoquinolin-1(2H)-one (50 mg) was combined with 0.600 mL of POCl3, and the reaction was stirred at 90 C for 1 h. After cooling, the reaction was partitioned between saturated aqueous sodium bicarbonate and EtOAc. The organic solution was dried over Na2SO4 and concentrated. Flash chromatography (3% MeOH in CH2Cl2) gave the titled compound.

Workup

  1. temperatureAfter cooling
  2. customthe reaction was partitioned between saturated aqueous sodium bicarbonate and EtOAc
  3. dry with materialThe organic solution was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1946815f0b0243388838f3a99a4baa43
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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