Phosphorus oxychloride → HCID 71742711, compound

HRID 2361602Notes

Reaction equation

HRID 2361602 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([O:13][CH3:14])=[CH:5][NH:6][C:7]2=O.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:7]1[C:8]2[C:3](=[C:2]([Cl:1])[CH:11]=[CH:10][CH:9]=2)[C:4]([O:13][CH3:14])=[CH:5][N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 70978316HCID 70978316, compound

Product 1

HCID 71742711HCID 71742711, compoundYield 57.4%

Procedure

A solution of 5-chloro-4-methoxyisoquinolin-1-(2H)-one (6.4 g, 30.5 mmol) in POCl3 (45 ml) was refluxed for 18 h. The solvent was evaporated under reduced pressure and the residue was diluted with cold water. The precipitated solid was filtered, washed with water to get crude compound (4 g, 57.4%) as a light brown colored solid. 1H NMR (400 MHz, CDCl3): δ ppm 8.28-8.25 (d, J=12 Hz, 1H), 7.87 (s, 1H), 7.79-7.76 (d, J=12 Hz, 1H), 7.58-7.54 (m, 1H), 4.03 (s, 3H); MS: MS m/z 228.0 (M++1).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with cold water
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-9829c17e642d4dc4b320e651b964a3d6
Source dataset
uspto-grants-2014_04
Patent number
US08691757B2

Reaction notes

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