2-Amino-5-chlorobenzophenone → HCID 46214902, compound

HRID 1184027Notes

Reaction equation

HRID 1184027 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.O=[C:18]([CH3:31])[CH2:19][C:20]([O:22][C@@H:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH3:24])=[O:21].[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.C(OCC)C>[Cl:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[N:1]=[C:18]([CH3:31])[C:19]([C:20]([O:22][C@@H:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH3:24])=[O:21])=[C:9]2[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 128702-Amino-5-chlorobenzophenoneHCID 2733225Ytterbium triflateHCID 11513976HCID 11513976, compound

Product 1

HCID 46214902HCID 46214902, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of (2-amino-5-chlorophenyl)(phenyl)methanone (1.16 g, 5.0 mmol) in ethanol (20 ml) was added (R)-1-phenylethyl 3-oxobutanoate (1.3 g, 6.5 mmol) followed by ytterbium triflate (294 mg, 0.5 mmol). The mixture was stirred at room temperature for 12 hours, then the ethanol was removed under reduced pressure, and the residual viscous oil dissolved in ethyl acetate. The organic phase was poured into a separatory funnel and washed with 1M aqueous hydrochloric acid, water, then brine. The organic phase was seoarated, and the solvent was removed under reduced pressure to provide a viscous oil. This was dissolved in a small amount of diethyl ether, and the solution allowed to stand at room temperature overnight. The white precipitate formed was filtered, washed with cold diethyl ether, and dried under reduced pressure, to provide (R)-1-phenylethyl 6-chloro-2-methyl-4-phenylquinoline-3-carboxylate (1.33 g, 67%) as a white powder. Rf=0.26 using 80:20 hexanes:ethyl acetate eluent on glass backed silica gel plates. 1H NMR (CDCl3, 400 MHz) δ 8.98 (d, 1H, J=8.9 Hz); 7.96 (d, 1H, J=7.4 Hz); 7.72 (d, 1H, J=1.95 Hz); 7.6-7.1 (m, 10H); 5.88 (q, 1H, J=6.6 Hz); 3.05 (s, 3H); 1.3 (d, 3H, J=6.6 Hz). LC MS (CI) shows M+H 402.

Workup

  1. customthe ethanol was removed under reduced pressure
  2. dissolutionthe residual viscous oil dissolved in ethyl acetate
  3. additionThe organic phase was poured into a separatory funnel
  4. washwashed with 1M aqueous hydrochloric acid, water
  5. customthe solvent was removed under reduced pressure
  6. customto provide a viscous oil
  7. waitto stand at room temperature overnight
  8. customThe white precipitate formed
  9. filtrationwas filtered
  10. washwashed with cold diethyl ether
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-fcd71652c4d34cc8ae6151e876455242
Source dataset
uspto-grants-2014_03
Patent number
US08664399B2

Reaction notes

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