Phosphorus oxychloride → HCID 71742711, compound

HRID 1852261Notes

Reaction equation

HRID 1852261 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-c9c1c86649a941c09efa79b9a4d97936
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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