Hydrochloric Acid → HCID 21105746, compound

HRID 1354465Notes

Reaction equation

HRID 1354465 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][C:14]=3[N+:23]([O-:25])=[O:24])[O:10][N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1.Cl>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=3[N+:23]([O-:25])=[O:24])[O:10][N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22934569HCID 22934569, compound

Product 1

HCID 21105746HCID 21105746, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 4-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]-3-nitrobenzoate (1.20 g), 1 M aqueous sodium hydroxide solution (6.6 ml) and tetrahydrofuran (10 ml) was heated under reflux for 30 min. After cooling, the reaction mixture was poured into water, and 1 M hydrochloric acid was added to acidify the mixture. The crystals were collected by filtration to give 4-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]-3-nitrobenzoic acid (1.10 g, yield 96%). Recrystallization from hexane-tetrahydrofuran gave colorless prism crystals. melting point: 257–258° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 min
  3. temperatureAfter cooling
  4. additionwas added
  5. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-db13b5e0b6e446cc94630052954eaec8
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

Loading…