Aniline → N-phenylquinolin-3-amine

HRID 2175456Notes

Reaction equation

HRID 2175456 reaction equation
[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

Participants

6

Reactant 3

HCID 6115AnilineHCID 796192-QuinolinecarboxaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 11117560N-phenylquinolin-3-amine

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5174dc4e06d444248492c68de7413b30
Source dataset
uspto-grants-2015_06
Patent number
US09062072B2

Reaction notes

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