Ethanol → (2-Methoxy-[1,1'-biphenyl]-4-yl)methanamine

HRID 1713281Notes

Reaction equation

HRID 1713281 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][N:10]2C(=O)C3=CC=CC=C3C2=O)[CH:6]=[CH:5][C:4]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)C>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH2:10])[CH:6]=[CH:5][C:4]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 67453881HCID 67453881, compound

Product 1

HCID 23143909(2-Methoxy-[1,1'-biphenyl]-4-yl)methanamineYield 100.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N-(2-methoxybiphenyl-4-ylmethyl)-phthalimide (0.414 g) in chloroform (5.0 mL) was added dropwise a mixture of hydrazinemonohydrate (0.241 g) and ethanol (1.0 mL), and the resulting mixture was stirred at room temperature for 31 hours. The insoluble material was filtered out, and the filtrate was partitioned between dichloromethane (40 mL) and water (15 mL). The organic layer was washed with brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (0.259 g).

Workup

  1. filtrationThe insoluble material was filtered out
  2. customthe filtrate was partitioned between dichloromethane (40 mL) and water (15 mL)
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-82a565650c1c4da389c3d0116156fb3f
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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