Ethanol → [1,1'-Biphenyl]-4-amine, 3-nitro-

HRID 1375289Notes

Reaction equation

HRID 1375289 reaction equation
[OH-].[K+].[N+:3]([C:6]1[CH:7]=[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=[CH:10][C:11]=1[NH:12]C(=O)C)([O-:5])=[O:4].C(O)C>O>[N+:3]([C:6]1[CH:7]=[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=[CH:10][C:11]=1[NH2:12])([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 79364Acetamide, N-(3-nitro(1,1'-biphenyl)-4-yl)-2×

Product 1

HCID 77705[1,1'-Biphenyl]-4-amine, 3-nitro-Yield 71.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of potassium hydroxide (2.5 g), 3-nitro-4-acetamido-1,1′-biphenyl (23.5 g), prepared in (A) above, water (6 mL) and ethanol (12 mL) is heated at reflux for one hour. The reaction mixture is cooled to room temperature and then poured into 300 mL of a mixture of water and ice. The solid is collected by filtration and the crude product is recrystallized from methanol (800 mL) to give 14.1 g of the title compound as an orange solid melting at 170–172° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for one hour
  3. filtrationThe solid is collected by filtration
  4. customthe crude product is recrystallized from methanol (800 mL)

Sources & evidence

ORD record
ord-c9fc43a7127d4e1384a776d4176ae517
Source dataset
uspto-grants-2007_01
Patent number
US07166659B2

Reaction notes

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