Calcium Chloride → N-(5-amino-4'-methoxybiphenyl-3-yl)acetamide

HRID 64134Notes

Reaction equation

HRID 64134 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[C:11]([NH:18][C:19](=[O:21])[CH3:20])[CH:10]=2)=[CH:5][CH:4]=1.[Cl-].[Ca+2].[Cl-]>C(O)C.[Fe]>[NH2:15][C:13]1[CH:12]=[C:11]([NH:18][C:19](=[O:21])[CH3:20])[CH:10]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH:14]=1

Participants

5

Reactant 2

HCID 5284359Calcium ChlorideHCID 89500151N-(4'-methoxy-5-nitrobiphenyl-3-yl)acetamide

Product 1

HCID 89500101N-(5-amino-4'-methoxybiphenyl-3-yl)acetamideYield 87%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-(4′-methoxy-5-nitrobiphenyl-3-yl)acetamide (4 g, 13.98 mmol) in ethanol (50 ml) were added calcium chloride (3.1 g, 27.96 mmol, 2 eq.) and iron powder (1.45 g, 27.96 mmol, 2 eq.) and the mixture was heated at 100° 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 87% yield (3.1 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 87% yield (3.1 g)

Sources & evidence

ORD record
ord-2466cabf962a464c8397abc5d9bda431
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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