2-Amino-5-chlorobenzophenone → Ethyl 6-chloro-2-(chloromethyl)-4-phenyl-3-quinolinecarboxylate

HRID 538743Notes

Reaction equation

HRID 538743 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.[Cl:17][CH2:18][C:19](=O)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>C(O)C>[Cl:16][C:13]1[CH:12]=[C:3]2[C:2](=[CH:15][CH:14]=1)[N:1]=[C:19]([CH2:18][Cl:17])[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:4]2[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 128702-Amino-5-chlorobenzophenoneHCID 69484Ethyl 4-chloroacetoacetateHCID 2733225Ytterbium triflate

Product 1

HCID 14417743Ethyl 6-chloro-2-(chloromethyl)-4-phenyl-3-quinolinecarboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a yellow solution of 2-amino-5-chlorobenzophenone (6.93 g, 30.0 mmol) in ethanol (150 ml) was added ethyl 4-chloroacetoacetate (5.3 ml, 39.0 mmol) followed by ytterbium triflate (1.6 g, 3.0 mmol). The mixture was stirred at room temperature for 48 hours, at which time a voluminous white suspension was noted. The mixture was filtered, and the precipitate washed with ethanol, then diethyl ether, to provide ethyl 6-chloro-2-(chloromethyl)-4-phenylquinoline-3-carboxylate as a white powder (93%). 1H NMR (CDCl3; 400 MHz) δ 8.08 (d, 1H, J=8.9 Hz); 7.71 (dd, 1H, J=8.9, 2.3 Hz); 7.59 (d, 1H, J=1.95 Hz); 7.54 (m, 3H); 7.38-7.30 (m, 2H); 5.0 (s, 2H); 4.05 (q, 2H, J=7.0 Hz); 0.92 (t, 3H, J=7.0 Hz). LC MS (CI) shows M+H 360.

Workup

  1. filtrationThe mixture was filtered
  2. washthe precipitate washed with ethanol

Sources & evidence

ORD record
ord-4bfe5dce56db472ba83e0f4863216bb3
Source dataset
uspto-grants-2014_10
Patent number
US08865739B2

Reaction notes

Loading…