Hydrochloric Acid → 2-amino-3-methylbiphenyl

HRID 1995137Notes

Reaction equation

HRID 1995137 reaction equation
[CH3:1][C:2]1[C:3]([N+:14]([O-])=O)=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:3]=1[NH2:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 140439853-Methyl-2-nitro-1,1'-biphenyl

Product 1

HCID 6030842-amino-3-methylbiphenyl

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

During a 45 minute period 3-methyl-2-nitro-[1,1'-biphenyl] (25.4 g, 0.119 mole) was added portionwise at 30° to a stirred solution of stannous chloride (107.5 g, 0.476 mole) and 150 ml of concentrated hydrochloric acid in enough ethanol to produce a solution. After complete addition the mixture was heated at reflux for 17 hours. The mixture was cooled and made basic (pH 9-10) with 4 N aqueous sodium hydroxide, producing a white precipitate. The precipitate was collected by filtration and partitioned between water and methylene chloride. The organic phase was separated, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated to give 3-methyl-[1,1'-biphenyl]-2-amine as a yellow oil.

Workup

  1. customto produce a solution
  2. additionAfter complete addition the mixture
  3. temperaturewas heated
  4. temperatureat reflux for 17 hours
  5. temperatureThe mixture was cooled
  6. customproducing a white precipitate
  7. filtrationThe precipitate was collected by filtration
  8. custompartitioned between water and methylene chloride
  9. customThe organic phase was separated
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-68a56131d7984fa491edfc1706e2cc0a
Source dataset
uspto-grants-1983_09
Patent number
US04402973

Reaction notes

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