Oxalyl chloride → HCID 178468829, compound

HRID 2357533Notes

Reaction equation

HRID 2357533 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[OH:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=3[CH3:27])[C:21](O)=[O:22])=[CH:15][CH:16]=2)[CH:11]=[N:10][N:9]=1>>[OH:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=3[CH3:27])[C:21]([O:5][CH2:1][CH3:2])=[O:22])=[CH:15][CH:16]=2)[CH:11]=[N:10][N:9]=1

Participants

3

Reactant 2

HCID 65578Oxalyl chlorideHCID 178425877HCID 178425877, compound

Product 1

HCID 178468829HCID 178468829, compoundYield 99.1%

Conditions

Temperature
0 °C

Procedure

To a 250 mL dry flask containing anhydrous ethanol (50 mL) stirred at 0° C. was added dropwise oxalyl chloride (54 mmol). After 5 minutes 3-(1-hydroxyphthalazin-6-yl)-4-methylbenzoic acid (18 mmol) was added in one portion, the suspension was warmed up to reflux and stirred for 3 h. The solvent was evaporated and the residue was vacuum dried at RT for about 2 h to give ethyl 3-(1-hydroxyphthalazin-6-yl)-4-methylbenzoate 5.5 g as an off white solid.

Workup

  1. customTo a 250 mL dry flask
  2. additioncontaining anhydrous ethanol (50 mL)
  3. temperaturethe suspension was warmed up
  4. temperatureto reflux
  5. stirringstirred for 3 h
  6. customThe solvent was evaporated
  7. customdried at RT for about 2 h

Sources & evidence

ORD record
ord-bfd3fcf3ad3f4296b2a1d17d229f2f64
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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