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

HRID 1465801

Reaction equation

HRID 1465801 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].[CH3:12][NH:13][CH3:14]>C(O)C>[CH3:12][N:13]([CH3:14])[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7]

Participants

4

Reactant 2

HCID 674Dimethylamine2×HCID 742185-Chloro-2-nitroaniline

Product 1

HCID 27334513-Amino-N,N-dimethyl-4-nitroanilineYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-chloro-2-nitroaniline (4.14 g, 24.0 mmol) in ethanol (62 ml) in a sealed thick-walled tube, was added aqueous 40% dimethylamine solution (22.5 ml, 178 mmol, 7.4 eq) and the mixture heated in a 90° C. oil-bath for 2 days (CAUTION: High pressure). After cooling, additional 40% dimethylamine solution (7.5 ml) was added and heating continued for a further 3 days. The reaction mixture was cooled to room temperature and the contents were tipped onto ice (250 ml). After stirring the suspension was filtered, washed with water (200 ml) and dried under vacuum to give 5-dimethylamino-2-nitroaniline as a bright yellow solid (4.16 g, 96%), mp 138.5-139.8° C. (lit. (8) mp 140° C.).

Workup

  1. temperatureAfter cooling
  2. temperatureheating
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationwas filtered
  5. washwashed with water (200 ml)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-dc3d02c093834155bc6c1f51c859e3aa
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Linked notes

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