Aniline → N-phenylquinolin-3-amine

HRID 2175456ノート

反応式

HRID 2175456 の反応式
[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

参加物

6

反応物 3

HCID 6115AnilineHCID 796192-QuinolinecarboxaldehydeHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 11117560N-phenylquinolin-3-amine

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5174dc4e06d444248492c68de7413b30
出典データセット
uspto-grants-2015_06
特許番号
US09062072B2

反応ノート

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