Sodium Carbonate → 1,3-Dichloroisoquinoline

HRID 1006876

Reaction equation

HRID 1006876 reaction equation
[C:1]1(=O)[NH:6][C:5](=O)[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]2[CH2:2]1.[Cl-:13].[Cl-:14].C1(P(=O)([O-])[O-])C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:13][C:5]1[C:4]2[C:3](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:2]=[C:1]([Cl:14])[N:6]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 3494351,3(2H,4H)-isoquinolinedioneHCID 22048082HCID 22048082, compound

Product 1

HCID 2986251,3-Dichloroisoquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture solution of homophthalimide (10.5 g) and phenylphosphonate dichloride (30 ml) was heated at 110° C. for 2 hr. After the reaction mixture was cooled, water was added thereto, and then the resulting mixture was neutralized with sodium carbonate. The resulting mixture was extracted with ethyl acetate, washed with brine, dried, and then the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (methylene chloride), to give 9.30 g of the title compound as white crystals.

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. customdried
  5. customthe solvent was evaporated
  6. customThe resulting residue was purified by silica gel column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-6979a33c740f4041a597c027f56fc455
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Linked notes

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