Aniline → Methyl 4'-(anilinomethyl)biphenyl-2-carboxylate

HRID 1186028Notes

Reaction equation

HRID 1186028 reaction equation
[C:1]1([NH2:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)=O.[BH4-].[Na+].[OH-].[Na+]>CO>[NH:7]([CH2:8][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 4325150Methyl 2-(4-formylphenyl)benzoate

Product 1

HCID 58657357Methyl 4'-(anilinomethyl)biphenyl-2-carboxylateYield 78.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Phenylamine (56 mg) was added to the compound (120 mg) prepared in Example 4 in methanol solution (3 mL) and stirred for 4 hours at room temperature. The reaction mixture was added to sodium borohydride (37 mg) and stirred for 1.5 hours. To alkalinize, 5 mol/L sodium hydroxide solution was added to the concentrated reaction mixture and then extracted with ethyl acetate. The organic layer was washed with saturated sodium and dried by anhydrous sodium sulfate, and then concentrated to obtain the titled compound (124 mg) having the following physical data by purifying the obtained residue by silica gel column chromatography (diethyl ether:hexane=1:2).

Workup

  1. stirringstirred for 1.5 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium
  4. dry with materialdried by anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-63a9cc8785114d36b6616ce77c0fbeaf
Source dataset
uspto-grants-2014_03
Patent number
US08673889B2

Reaction notes

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