Ammonia → 2-(4-Amino-3-nitrophenyl)-3-chloro-5-trifluoromethylpyridine

HRID 1276087Notes

Reaction equation

HRID 1276087 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15](F)=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[NH3:22]>O1CCCC1>[NH2:22][C:15]1[CH:16]=[CH:17][C:12]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][N:4]=2)=[CH:13][C:14]=1[N+:19]([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 221148423-Chloro-2-(4-fluoro-3-nitrophenyl)-5-(trifluoromethyl)pyridine

Product 1

HCID 221148472-(4-Amino-3-nitrophenyl)-3-chloro-5-trifluoromethylpyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 50.0 g of 3-chloro-2-(4-fluoro-3-nitrophenyl)-5-trifluoromethylpyridine in 200 ml of tetrahydrofuran was treated with 200 g of a 25% strength by weight aqueous ammonia solution. After stirring at 23° C. for three days, the tetrahydrofuran was removed by distillation, whereupon the product crystallized. The crystals were separated off, washed with water and dried in a vacuum drying oven. Yield: 48.7 g (98%) of colorless crystals; m.p.: 126-127° C.

Workup

  1. customthe tetrahydrofuran was removed by distillation, whereupon the product
  2. customcrystallized
  3. customThe crystals were separated off
  4. washwashed with water
  5. customdried in a vacuum
  6. customdrying oven

Sources & evidence

ORD record
ord-fbebe323c4434000845bf9cca13a9365
Source dataset
uspto-grants-2000_12
Patent number
US06165941

Reaction notes

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