Aniline → N-phenylquinolin-3-amine

HRID 2175456노트

반응식

HRID 2175456 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1C=O.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[BH3-]C#N.[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[C:14]1([NH:13][C:3]2[CH:2]=[N:1][C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

6

반응물 3

HCID 6115AnilineHCID 796192-QuinolinecarboxaldehydeHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 11117560N-phenylquinolin-3-amine

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 887Methanol용매

실험 절차

To a solution of quinoline-3-carbaldehyde 11 (79 mg, 0.5 mmol) in MeOH (5 mL) was added aniline (0.05 mL, 0.55 mmol) and ZnCl2 (136 mg, 2.0 mmol) and the reaction was stirred at room temperature for 15 min. Then NaCNBH3 (62.8 mg, 2.0 mmol) was added and to the reaction was stirred overnight at room temperature. The solvent was removed by rotary evaporation and the residue suspended in EtOAc. The organic layers were combined and washed with NaHCO3, water, and brine and then dried over MgSO. Concentration in vacuo gave the crude product, which was used in the next step without further purification. 1H NMR (CDCl3): 9.05 (s, 1H), 8.23 (d, J=7.6 Hz, 2H), 7.77 (d, J=8.0 Hz, 1H), 7.71-7.66 (m, 1H), 7.54-7.51 (m, 1H), 7.21-7.16 (m, 2H), 6.76-6.72 (m, 1H), 6.68-6.60 (m, 2H), 4.54 (s, 2H), 4.16 (s, br, 1H).

후처리

  1. stirringwas stirred overnight at room temperature
  2. customThe solvent was removed by rotary evaporation
  3. washwashed with NaHCO3, water, and brine
  4. dry with materialdried over MgSO
  5. concentrationConcentration in vacuo

출처 및 근거

ORD 기록
ord-5174dc4e06d444248492c68de7413b30
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062072B2

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