Ethanol → 3-Chloro-5-(4-methyl-piperazin-1-yl)-benzoic acid

HRID 1946256Notes

Reaction equation

HRID 1946256 reaction equation
[Cl:1][C:2]1[CH:3]=C([CH:7]=[C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[CH:9]=1)C#N.[OH-:17].[Na+].[CH2:19]([OH:21])[CH3:20]>Cl>[Cl:1][C:2]1[CH:3]=[C:20]([CH:7]=[C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[CH:9]=1)[C:19]([OH:17])=[O:21]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 591389873-Chloro-5-(4-methyl-piperazin-1-yl)-benzonitrile

Product 1

HCID 591390453-Chloro-5-(4-methyl-piperazin-1-yl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 3-chloro-5-(4-methyl-piperazin-1-yl)-benzonitrile (1.4 g, 5.9 mmol) dissolved in ethanol (10 ml) was added 2M NaOH (20 ml) and reaction mixture was heated at reflux for 20 hours. The mixture was reduced in vacuo and the crude product was acidified in 1N HCl to pH 6 and partitioned between EtOAc and H2O. The organic layer was evaporated to dryness in vacuo to give 0.7 g of the title compound as a white solid (LC/MS: Rt 1.67, [M+H]+ 256, acidic method).

Workup

  1. additionwas added
  2. temperaturewas heated
  3. temperatureat reflux for 20 hours
  4. custompartitioned between EtOAc and H2O
  5. customThe organic layer was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-98c88d4299be47f993e5e71809f7e745
Source dataset
uspto-grants-2013_03
Patent number
US08399442B2

Reaction notes

Loading…