Dimethylamine → HCID 13596230, compound

HRID 325749Notes

Reaction equation

HRID 325749 reaction equation
[OH:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]([CH3:15])=[CH:8][C:3]=1[C:4](OC)=[O:5].[CH3:16][NH:17][CH3:18]>C(O)C>[CH3:16][N:17]([CH3:18])[C:4](=[O:5])[C:3]1[CH:8]=[C:9]([CH3:15])[CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 12571280Methyl 2-hydroxy-5-methyl-3-nitrobenzoate

Product 1

HCID 13596230HCID 13596230, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 2-hydroxy-5-methyl-3-nitrobenzoate (5.0 g) was dissolved in a solution of dimethylamine in ethanol (33% w/v; 50 ml) and the solution was heated at 100° C. in a sealed pressure vessel for 20 hours. The solvent was removed in vacuo and the residue was triturated with hydrochloric acid (2 N; 50 ml), and washed with water. Recrystallisation from methanol gave N,N-dimethyl-2-hydroxy-5-methyl-3-nitrobenzamide (3.0 g), m.p. 160°-162° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was triturated with hydrochloric acid (2 N; 50 ml)
  3. washwashed with water
  4. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-09ec44261cb2497680428cf5f4168180
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

Loading…