2-Amino-5-chlorobenzophenone → HCID 86682957, compound

HRID 1497099Notes

Reaction equation

HRID 1497099 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.[CH3:17][O:18][C:19](=[O:28])[CH2:20][C:21](=O)[CH2:22][C:23]([F:26])([F:25])[F:24].[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>[CH3:17][O:18][C:19]([C:20]1[C:21]([CH2:22][C:23]([F:24])([F:26])[F:25])=[N:1][C:2]2[C:3]([C:9]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:4][C:5]([Cl:8])=[CH:6][CH:7]=2)=[O:28]

Participants

5

Reactant 3

HCID 128702-Amino-5-chlorobenzophenoneHCID 2733225Ytterbium triflateHCID 53408031Methyl 5,5,5-trifluoro-3-oxopentanoate

Product 1

HCID 86682957HCID 86682957, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2-amino-5-chloro-phenyl)-phenyl-methanone (120 mg, 0.52 mmol) and 5,5,5-trifluoro-3-oxo-pentanoic acid methyl ester (124 mg, 0.67 mmol) in 5 ml ethanol at room temperature was added ytterbium triflate (32 mg, 0.05 mmol). The reaction mixture was stirred for 16 h at room temperature, upon which a white precipitate was formed. The precipitated solid was filtered and washed with ethanol to afford 6-chloro-4-phenyl-2-(2,2,2-trifluoro-ethyl)-quinoline-3-carboxylic acid methyl ester (70 mg, 36%) as an off white solid. LC-MS: 380 (M+H)+.

Workup

  1. customwas formed
  2. filtrationThe precipitated solid was filtered
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-d98f7612771642f69d7387ff4c65f008
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

Loading…