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

HRID 1985675Notes

Reaction equation

HRID 1985675 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10](Cl)=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2].[CH3:14][NH:15][CH3:16]>>[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([N:15]([CH3:16])[CH3:14])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 172865-Chloro-2-nitrobenzoic acid

Product 1

HCID 127157935-(Dimethylamino)-2-nitrobenzoic acid

Conditions

Temperature
100 °C

Procedure

The mixture of 5 g of 2-nitro-5-chlorobenzoic acid and 15 mL of 60% aqueous dimethylamine solution is stirred at 100° C. for 6 hours. The reaction mixture is evaporated, the residue dissolved in 15 mL of water. The pH of the mixture is adjusted to 6 with acetic acid. The precipitated yellow crystalline material is filtered off, washed with water and dried, to obtain 3.4 g of the title compound. Mp.: 189° C.

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionthe residue dissolved in 15 mL of water
  3. filtrationThe precipitated yellow crystalline material is filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-e518c191459d42cdbd5f97a5274ed1f4
Source dataset
uspto-grants-2009_06
Patent number
US07547696B2

Reaction notes

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