Phosphorus oxychloride → HCID 86683220, compound

HRID 1852148Notes

Reaction equation

HRID 1852148 reaction equation
[CH2:1]([N:8]([CH3:22])[C:9]1[N:10]=[C:11](O)[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([O:19][CH3:20])=[CH:14][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:25]>>[CH2:1]([N:8]([CH3:22])[C:9]1[N:10]=[C:11]([Cl:25])[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([O:19][CH3:20])=[CH:14][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178487764HCID 178487764, compound

Product 1

HCID 86683220HCID 86683220, compoundYield 75%

Conditions

Temperature
0 °C

Procedure

A solution of 3-(benzyl(methyl)amino)-6-methoxyisoquinolin-1-ol (1.8 g, 6.12 mmol) in POCl3 (10 mL) was refluxed for 4 h. After concentration, the residue was taken into a mixture of 100 mL of DCM and 50 mL of water, cooled to 0° C., neutralized with 3 N NaOH, dried over MgSO4, and concentrated to give N-benzyl-1-chloro-6-methoxy-N-methylisoquinolin-3-amine (1.44 g, 4.60 mmol, 75% yield) as a yellow solid. MS: MS m/z 313.15(M++1).

Workup

  1. concentrationAfter concentration
  2. additionthe residue was taken into a mixture of 100 mL of DCM and 50 mL of water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8dea32731ee34e7e9f58b1170c99f93f
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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