Water → HCID 67450579, compound

HRID 1465829Notes

Reaction equation

HRID 1465829 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][N:13]([CH3:15])[NH2:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[CH3:12][N:13]([CH3:15])[NH:14][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:7])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 59761,1-DimethylhydrazineHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 67450579HCID 67450579, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 5-chloro-2-nitroaniline (20 g, 116 mmol), N,N-dimethyl-hydrazine (44 mL, 580 mmol) and anhydrous potassium carbonate (17.6 g, 128 mmol) in N,N-dimethylacetamide (50 ml) were stirred at 125° C. under nitrogen for 3 days Sample NMR analysis showed complete conversion of the starting material. The resultant mixture was then cooled to room temperature, poured onto cold water (400 mL), stirred vigorously and incubated at 4° C. overnight. The resulting brown precipitate was collected by filtration, washed well with water then dried on the filter funnel. This was then slurried in diethyl ether, filtered, washed with additional diethyl ether, dried to afford 5-(N′,N′-Dimethyl-hydrazino)-2-nitro-phenylamine (10.7 g, 47% yield) as a yellow solid. The crude product was used in the next step without further purification.

Workup

  1. stirringstirred vigorously
  2. waitincubated at 4° C. overnight
  3. filtrationThe resulting brown precipitate was collected by filtration
  4. washwashed well with water
  5. customthen dried on the filter funnel
  6. filtrationfiltered
  7. washwashed with additional diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-1b4009faddfc4a82852fdbf65936e31d
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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