Hydrochloric Acid → 2-(dimethylamino)-5-nitrobenzoic acid

HRID 450073Notes

Reaction equation

HRID 450073 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14][NH:15][CH3:16].Cl>[OH-].[Na+]>[CH3:14][N:15]([CH3:16])[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 172872-Chloro-5-nitrobenzoic acid

Product 1

HCID 28046762-(dimethylamino)-5-nitrobenzoic acidYield 57%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2-Chloro-5-nitrobenzoic acid (2 g, 9.9 mmol) was dissolved in of 8% sodium hydroxide solution (10 ml) at room temperature. 40% dimethyl amine aqueous solution (1.5 eq) was added and the reaction mixture was heated to reflux for 3 days. The reaction mixture was neutralized with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was dried and evaporated and the residue crystallized with ether/pet ether to give 2-dimethylamino-5-nitro-benzoic acid (1.14 g, 57%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 3 days
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. customevaporated
  6. customthe residue crystallized with ether/pet ether

Sources & evidence

ORD record
ord-d211778ab7d8476597463296efa233ab
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

Loading…