Ammonia → 4-amino-N-[2,6-dichloro-4-(1,1,1,2,3,3,3-heptafluoro propan-2-yl)phenyl]benzamide

HRID 587846Notes

Reaction equation

HRID 587846 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([Cl:18])[C:3]=1[NH:19][C:20](=[O:30])[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=1.[BH4-].[Na+].N>CO.C(OCC)(=O)C.O.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:27][C:24]1[CH:23]=[CH:22][C:21]([C:20]([NH:19][C:3]2[C:4]([Cl:18])=[CH:5][C:6]([C:8]([F:17])([C:13]([F:14])([F:15])[F:16])[C:9]([F:10])([F:11])[F:12])=[CH:7][C:2]=2[Cl:1])=[O:30])=[CH:26][CH:25]=1

Participants

8

Reactant 3

HCID 222AmmoniaHCID 4311764Sodium borohydrideHCID 86666630N-[2,6-Dichloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-4-nitro-benzamide

Product 1

HCID 866666314-amino-N-[2,6-dichloro-4-(1,1,1,2,3,3,3-heptafluoro propan-2-yl)phenyl]benzamideYield 96.3%

Reagents, catalysts & solvents 4

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[2,6-Dichloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-4-nitro-benzamide (3.2 g) and nickel (II) chloride hexahydrate (3.33 g) were dissolved in methanol (30 ml). To the reaction solution, NaBH4 (0.80 g) was added slowly under ice cooling, and the mixture was stirred for 1 hour while increasing the temperature to room temperature. Aqueous ammonia (about 5 ml) was added to the reaction solution under stirring, and then diluted with ethyl acetate and water. The organic phase was separated and the aqueous layer was extracted with ethyl acetate. The organic phases were combined, and then dried over magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off under reduced pressure to obtain a crude product, which was then separated and purified by column chromatography to give 4-amino-N-[2,6-dichloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-benzamide (2.89 g, yield 96%).

Workup

  1. stirringunder stirring
  2. customThe organic phase was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto obtain a crude product, which
  8. customwas then separated
  9. custompurified by column chromatography

Sources & evidence

ORD record
ord-a72962ff76de426db384a23f83964399
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

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