Ammonium Chloride → N-(5-aminobiphenyl-3-yl)acetamide

HRID 64131Notes

Reaction equation

HRID 64131 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:16][C:17](=[O:19])[CH3:18])[CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:9]=1)([O-])=O.[Cl-].[NH4+]>C1COCC1.O.[Zn]>[NH2:1][C:4]1[CH:5]=[C:6]([NH:16][C:17](=[O:19])[CH3:18])[CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:9]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 89500237N-(5-nitrobiphenyl-3-yl)acetamide

Product 1

HCID 308689N-(5-aminobiphenyl-3-yl)acetamideYield 94%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of N-(5-nitrobiphenyl-3-yl)acetamide (1.2 g, 4.68 mmol) in THF (10 ml) were added a solution of ammonium chloride (2 g, 37.4 mmol, 8 eq.) in water (2 ml) and zinc (2.36 g, 37.4 mmol, 8 eq.). The mixture was stirred at 45° C. for 2 h and filtered. The filtrate was diluted with water and extracted as in Example 1(d). The solvent was distilled off to afford the product in 94% yield (1 g).

Workup

  1. filtrationfiltered
  2. additionThe filtrate was diluted with water
  3. extractionextracted as in Example 1(d)
  4. distillationThe solvent was distilled off
  5. customto afford the product in 94% yield (1 g)

Sources & evidence

ORD record
ord-acba007b2aea44e299dfd5be3b4dfb87
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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