Chlorine monoxide → 1,7-Dichloro-3-methylisoquinoline

HRID 1432852Notes

Reaction equation

HRID 1432852 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:13])[NH:8][C:9]2=O)=[CH:4][CH:3]=1.O(Cl)[Cl:15]>>[Cl:15][C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:11]=2)[CH:6]=[C:7]([CH3:13])[N:8]=1

Participants

3

Reactant 2

HCID 24646Chlorine monoxideHCID 230846567-Chloro-3-methyl-1(2H)-isoquinolinone

Product 1

HCID 213880331,7-Dichloro-3-methylisoquinoline

Procedure

A solution of 7-chloro-3-methyl-2H-isoquinoline-1-one (7.1 g, 36.7 mmol) in 100 mL of phosporous oxychloride is heated to 100° C. After 5 h, the solution is concentrated to dryness. The residue is dissolved in CH2Cl2. The solution is washed with H2O. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with a gradient of 3% EtOAc/hexanes to 5% EtOAc/hexanes. The title compound is obtained as a white solid (6.0 g, 28 mmol). 1H NMR (CDCl3, 300 MHz) δ8.23 (s, 1H), 7.68 (m, 1H), 7.63 (m, 1H), 7.40 (s, 1H), 2.64 (s, 3H).

Workup

  1. concentrationthe solution is concentrated to dryness
  2. dissolutionThe residue is dissolved in CH2Cl2
  3. washThe solution is washed with H2O
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by column chromatography
  8. washeluting with a gradient of 3% EtOAc/hexanes to 5% EtOAc/hexanes

Sources & evidence

ORD record
ord-5c72f8ccd0dc46f3b7fa0f57a18a6278
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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