Hydrochloric Acid → HCID 22467532, compound

HRID 1934661Notes

Reaction equation

HRID 1934661 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:7]([CH:12]=1)[C:8]([O:10]C)=[O:9])#[N:2].[OH-].[Na+].Cl>CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:7]([CH:12]=1)[C:8]([OH:10])=[O:9])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22467350HCID 22467350, compound

Product 1

HCID 22467532HCID 22467532, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 5-cyano-2-(cyclopentylamino)benzoate (2.30 g), methanol (100 mL) and 1N-sodium hydroxide solution (20 mL) was heated for 2 hours under reflux. The reaction mixture was acidified with 1N-hydrochloric acid to pH 4 and the organic solvent was removed by evaporation. The aqueous layer was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over magnesium sulfate. Then, the resultant was evaporated in vacuo to give 5-cyano-2-(cyclopentylamino)benzoic acid (2.15 g) as pale yellow powders.

Workup

  1. temperaturewas heated for 2 hours
  2. temperatureunder reflux
  3. customthe organic solvent was removed by evaporation
  4. additionThe aqueous layer was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customThen, the resultant was evaporated in vacuo

Sources & evidence

ORD record
ord-d0eac8a87b6448ddac311e43d8d28bfa
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

Loading…