2-Chloro-3,5-dinitropyridine → N-(2H-1,3-Benzodioxol-5-yl)-3,5-dinitropyridin-2-amine

HRID 614348Notes

Reaction equation

HRID 614348 reaction equation
[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[O:2]1.Cl[C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:15]([N+:21]([O-:23])=[O:22])=[CH:14][N:13]=1>CO>[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH:6][C:12]3[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:15]([N+:21]([O-:23])=[O:22])=[CH:14][N:13]=3)=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 2

HCID 757382-Chloro-3,5-dinitropyridineHCID 843101,3-Benzodioxol-5-amine

Product 1

HCID 21329304N-(2H-1,3-Benzodioxol-5-yl)-3,5-dinitropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 12.0 g. (0.0875 mole) of 3,4-methylenedioxyaniline in 100 ml. of methanol, was added with stirring 8.0 g. (0.04 mole) of 2-chloro-3,5-dinitropyridine. Within one minute the mixture had crystallized. To complete the reaction, the mixture was heated on a steam bath for 15 minutes, then cooled and filtered to give 11.0 g. of product. A small amount recrystallized from methanol melted at 187°-188° C.

Workup

  1. customWithin one minute the mixture had crystallized
  2. customthe reaction
  3. temperaturethe mixture was heated on a steam bath for 15 minutes
  4. temperaturecooled
  5. filtrationfiltered
  6. customto give 11.0 g
  7. customA small amount recrystallized from methanol melted at 187°-188° C.

Sources & evidence

ORD record
ord-306faf7157a5476680f9b9189b42a204
Source dataset
uspto-grants-1979_03
Patent number
US04144341

Reaction notes

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