Ammonium Chloride → HCID 89500232, compound

HRID 64088Notes

Reaction equation

HRID 64088 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:10]=[C:11]([NH:23][C:24](=[O:26])[CH3:25])[CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=3[F:22])[CH:14]=2)=[C:4]([N+:27]([O-])=O)[CH:3]=1.[Cl-].[NH4+]>C1COCC1.O.[Zn]>[NH2:27][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[NH:8][C:9]1[CH:10]=[C:11]([NH:23][C:24](=[O:26])[CH3:25])[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[CH:14]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 89500227N-(5-(4-bromo-2-nitrophenylamino)-2',4'-difluorobiphenyl-3-yl)acetamide

Product 1

HCID 89500232HCID 89500232, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(5-(4-bromo-2-nitrophenylamino)-2′,4′-difluorobiphenyl-3-yl)acetamide (3.2 g, 6.92 mmol) in THF (30 ml) were added a solution of ammonium chloride (3.7 g, 69.22 mmol, 10 eq.) in water (15 ml) and zinc (4.53 g, 69.22 mmol, 10 eq.). The mixture was stirred at RT for 6 h and filtered. The filtrate was diluted with water and extracted as in Example 1(d). The solvent was distilled off under reduced pressure to afford the product in 87% yield (2.6 g).

Workup

  1. filtrationfiltered
  2. additionThe filtrate was diluted with water
  3. extractionextracted as in Example 1(d)
  4. distillationThe solvent was distilled off under reduced pressure
  5. customto afford the product in 87% yield (2.6 g)

Sources & evidence

ORD record
ord-52208a378b5f4af1938d296a47591f3f
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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