Benzene → HCID 13187643, compound

HRID 326017Notes

Reaction equation

HRID 326017 reaction equation
S(Cl)([Cl:3])=O.O[CH:6]([CH3:25])[CH2:7][N:8]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:24].C(N(CC)CC)C.C1C=CC=CC=1>O>[Cl:3][CH:6]([CH3:25])[CH2:7][N:8]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:24]

Participants

6

Reactant 4

HCID 241BenzeneHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 131876422-(2-hydroxypropyl)-4-phenyl-1(2H)-isoquinolone

Product 1

HCID 13187643HCID 13187643, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

18 g of thionyl chloride was added dropwise to a mixture of 27.9 g of 2-(2-hydroxypropyl)-4-phenyl-1(2H)-isoquinolone prepared as described above, 11.1 g of triethylamine and 200 ml of benzene and then the resulting mixture was stirred at 50° to 60° C. for 1 hour. After allowing the mixture to cool, water was added to the mixture which was then thoroughly shaked. The benzene layer was separated and dried over sodium sulfate. The solvent was distilled off, and the resulting crystals were recrystallized from a mixture of chloroform and petroleum ether to obtain 25.3 g (85% yield) of 2-(2-chloropropyl)-4-phenyl-1(2H)-isoquinolone having a melting point of 141° C. as colorless needles.

Workup

  1. customprepared
  2. temperatureto cool
  3. customThe benzene layer was separated
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe resulting crystals were recrystallized from a mixture of chloroform and petroleum ether

Sources & evidence

ORD record
ord-829a641487b942e1bc2bbbf2b19a029c
Source dataset
uspto-grants-1984_04
Patent number
US04443607

Reaction notes

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