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

HRID 1186028노트

반응식

HRID 1186028 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-63a9cc8785114d36b6616ce77c0fbeaf
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673889B2

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