Phosphorus oxychloride → 4-Bromo-1-chloro-5-methylisoquinoline

HRID 1470456Notes

Reaction equation

HRID 1470456 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH3:12])[C:5](=O)[NH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:16]>>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH3:12])[C:5]([Cl:16])=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 183694934-Bromo-5-methylisoquinolin-1(2H)-one

Product 1

HCID 247661904-Bromo-1-chloro-5-methylisoquinolineYield 92%

Procedure

A stirred solution of 4-bromo-5-methylisoquinolin-1(2H)-one (Intermediate-4) (10 g, 42 mmol) in POCl3 (50 mL) was heated to 100° C. for 30 min. The reaction mixture was then poured into ice-water, extracted with CH2Cl2 (3×200 mL), washed with water (2×200 mL), dried over Na2SO4, filtered and concentrated to obtain desired compound (10 g, 92%).

Workup

  1. extractionextracted with CH2Cl2 (3×200 mL)
  2. washwashed with water (2×200 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-597f2e538e12429994caa428e357fffb
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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