Oxalyl chloride → HCID 20063329, compound

HRID 1084449Notes

Reaction equation

HRID 1084449 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[N:10]([CH:19]([CH3:21])[CH3:20])[C:9]=2/[CH:22]=[CH:23]/[C:24]([OH:26])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:30])=O>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[N:10]([CH:19]([CH3:21])[CH3:20])[C:9]=2/[CH:22]=[CH:23]/[C:24]([Cl:30])=[O:26])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 19778163HCID 19778163, compound

Product 1

HCID 20063329HCID 20063329, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (E)-3-[4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl]prop-2-enoic acid (0.35 g) in dry tetrahydrofuran (10 ml) was treated with oxalyl chloride (0.26 ml) and heated at reflux for 2 hours. The solvent was then removed by distillation and the residual yellow solid was washed with petroleum ether (b.p. 40°-60° C.), to give (E)-3-[4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl]prop-2-enoyl chloride in the form of a pale yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was then removed by distillation
  4. washthe residual yellow solid was washed with petroleum ether (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-7389806d9221485b82aa504164296330
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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