Malononitrile → 2-amino-6-chloro-4-phenylquinoline-3-carbonitrile

HRID 538746Notes

Reaction equation

HRID 538746 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[C:17](#[N:21])[CH2:18][C:19]#[N:20].[O-]CC.[Na+]>C(O)C>[NH2:21][C:17]1[C:18]([C:19]#[N:20])=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]2[C:2](=[CH:15][CH:14]=[C:13]([Cl:16])[CH:12]=2)[N:1]=1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 128702-Amino-5-chlorobenzophenoneHCID 2723922Sodium ethoxide

Product 1

HCID 2686042-amino-6-chloro-4-phenylquinoline-3-carbonitrileYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a yellow solution of 2-amino-5-chlorobenzophenone (2.31 g, 10.0 mmol) in warm (82° C.) dry ethanol (20 ml) was added malononitrile (1.98 g, 30.0 mmol) followed by a solution of sodium ethoxide (9.6 ml of a 3.08 M solution in ethanol, 30.0 mmol). The reaction was heated at reflux for 48 hours, then cooled to room temperature, and the solid filtered off, which was washed with water, ethyl acetate, and dried under reduced pressure to provide 2-amino-6-chloro-4-phenylquinoline-3-carbonitrile as a yellow powder (2.44 g, 87% yield). TLC Rf=0.62 using 1:1 ethyl acetate:hexanes on a silica gel glass backed plate. 1H NMR (DMSO-d6; 400 MHz) δ 7.70-7.58 (m, 5H); 7.56-7.5 (m, 2H); 7.22-7.12 (m, 3H). LC MS (CI) shows M+H 280.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 48 hours
  3. filtrationthe solid filtered off
  4. washwhich was washed with water, ethyl acetate
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-cd99a2f36494497ba281fa3e4576b39b
Source dataset
uspto-grants-2014_10
Patent number
US08865739B2

Reaction notes

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