Phosphorus oxychloride → 1-Chloro-7-methylisoquinoline

HRID 1171057Notes

Reaction equation

HRID 1171057 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2O)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([CH3:1])[CH:11]=2)[CH:6]=[CH:7][N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178422833HCID 178422833, compound

Product 1

HCID 222501861-Chloro-7-methylisoquinolineYield 85%

Procedure

The solution of POCl3 (10 mL) and 7-methyl-isoquinolin-1-ol (3.55 g, 22.3 mmol) was refluxed under nitrogen for 5 h. The residue, after removal of POCl3 by distillation, was quenched with iced water and extracted with methylene chloride (3×). Purification by flash silica gel column using 10-25% EtOAc in hexane as elute gave 3.40 g (85% yield) of desired product. 1H-NMR (300 MHz, CDCl3) δ 8.21 (d, 1H), 8.11 (s, 1H), 7.75 (d, 1H 7.60 (d, 1H), 7.55 (d, 1H), 2.60 (s, 3H).

Workup

  1. customThe residue, after removal of POCl3
  2. distillationby distillation
  3. customwas quenched with iced water
  4. extractionextracted with methylene chloride (3×)
  5. customPurification by flash silica gel column
  6. washas elute

Sources & evidence

ORD record
ord-ecbbe00a8c8a4816ba0a8984e5fa9fcd
Source dataset
uspto-grants-2010_11
Patent number
US07829584B2

Reaction notes

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