Dimethylamine → 2-(dimethylamino)-5-nitrobenzoic acid

HRID 450098Notes

Reaction equation

HRID 450098 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]>C(O)(=O)C>[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

4

Reactant 2

HCID 674DimethylamineHCID 172872-Chloro-5-nitrobenzoic acid

Product 1

HCID 28046762-(dimethylamino)-5-nitrobenzoic acidYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
62.5 °C

Procedure

2-Chloro-5-nitro benzoic acid (2 g, 10 mmol) was added to 40% dimethylamine aq. solution (20 ml) at room temperature and then heated at 60-65° C. for 3 hr. The reaction mixture was chilled to 0° C. and acidified with dilute acetic acid. The mixture was then extracted with ethyl acetate, and the organic layer washed with water, then brine and dried. Evaporation of the solvent yielded 2-dimethylamino-5-nitro-benzoic acid (2.1 g, 91%), as a solid.

Workup

  1. temperatureThe reaction mixture was chilled to 0° C.
  2. extractionThe mixture was then extracted with ethyl acetate
  3. washthe organic layer washed with water
  4. dry with materialbrine and dried
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a94c41b4686b4b76be8b7d7aaf3fc7ae
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

Loading…