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

HRID 655692Notes

Reaction equation

HRID 655692 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-09535856978244ae89d2d6538f47b6e7
Source dataset
uspto-grants-2011_12
Patent number
US08071601B2

Reaction notes

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