Ethanol → 3-Amino-N,N-dimethyl-4-nitroaniline

HRID 1160165

Reaction equation

HRID 1160165 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].C(O)C.Cl.[CH3:16][NH:17][CH3:18]>C(N(CC)CC)C>[CH3:16][N:17]([CH3:18])[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7]

Participants

5

Reactant 3

HCID 702EthanolHCID 10473Dimethylamine, hydrochlorideHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 27334513-Amino-N,N-dimethyl-4-nitroanilineYield 17,390.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
130 °C

Procedure

5-Chloro-2-nitroaniline (50 g; 0.29 mol) was added to a 5 L bomb followed by ethanol (1.1 L) at 0-5° C. Dimethylamine hydrochloride (130 g; 1.59 mmol) was added in one portion followed by triethylamine (260 ml) and the bomb quickly sealed. The bomb was heated to 130° C. with stirring at 4 bar for 20 hours. The reaction mixture was then allowed to cool to room temperature and the ethanol was removed under vacuum. 2 M sodium hydroxide solution (1 L) was added to the crude residue and this was extracted with ethyl acetate (1×1.3 L then 2×500 ml). The combined organic layers were washed with brine (150 ml), dried (magnesium sulphate), filtered and evaporated to give the 5-dimethylamino-2-nitroaniline (50.1 g, 96%).

Workup

  1. customthe bomb quickly sealed
  2. temperatureto cool to room temperature
  3. customthe ethanol was removed under vacuum
  4. addition2 M sodium hydroxide solution (1 L) was added to the crude residue
  5. extractionthis was extracted with ethyl acetate (1×1.3 L
  6. washThe combined organic layers were washed with brine (150 ml)
  7. dry with materialdried (magnesium sulphate)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-c8b6ce5c86484c9ca0828c6811396c04
Source dataset
uspto-grants-2010_10
Patent number
US07816369B2

Linked notes

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