Ethanol → N-(2H-1,3-Benzodioxol-5-yl)-6-fluoro-3-nitropyridin-2-amine

HRID 614356Notes

Reaction equation

HRID 614356 reaction equation
C(O)C.F[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([F:14])[N:6]=1.C(=O)(O)[O-].[Na+].[CH2:20]1[O:29][C:28]2[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][C:22]=2[O:21]1>O>[F:14][C:7]1[N:6]=[C:5]([NH:25][C:24]2[CH:26]=[CH:27][C:28]3[O:29][CH2:20][O:21][C:22]=3[CH:23]=2)[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 843101,3-Benzodioxol-5-amineHCID 516892Sodium BicarbonateHCID 113895462,6-Difluoro-3-nitropyridine

Product 1

HCID 21329326N-(2H-1,3-Benzodioxol-5-yl)-6-fluoro-3-nitropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 75 ml. of ethanol was dissolved 3.2 g. (0.002 mole) of 2,6-difluoro-3-nitropyridine followed by 1.68 g. (0.02 mole) of sodium bicarbonate. To this stirred mixture, was added a solution of 2.74 g. (0.02 mole) of 3,4-(methylenedioxy) aniline in 50 ml. of ethanol dropwise over 45 minutes at room temperature. After one hour, 100 ml. of water was added and the deep-red crystalline solid product was collected. A small amount was crystallized from ethanol and melted at 161°-162° C.

Workup

  1. additionTo this stirred mixture, was added a solution of 2.74 g
  2. customthe deep-red crystalline solid product was collected
  3. customA small amount was crystallized from ethanol and melted at 161°-162° C.

Sources & evidence

ORD record
ord-9d51f497891740dba38ac9927bb91192
Source dataset
uspto-grants-1979_03
Patent number
US04144341

Reaction notes

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