3-Chloropropiophenone → HCID 21837483, compound

HRID 1739830Notes

Reaction equation

HRID 1739830 reaction equation
Cl.C(OCC)C.[NH2:7][C:8]1[CH:22]=[CH:21][C:11]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[O:13])=[CH:10][CH:9]=1.Cl[CH2:24][CH2:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=O>C(O)C.[Cl-].[Cl-].[Zn+2]>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]([C:11]2[CH:21]=[C:22]3[C:8](=[CH:9][CH:10]=2)[N:7]=[CH:24][CH:25]=[C:26]3[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:13])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 702953-ChloropropiophenoneHCID 35287064-Amino-4'-chlorobenzophenoneHCID 10953452Ether hydrochloride

Product 1

HCID 21837483HCID 21837483, compoundYield 37.4%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 702EthanolSolvent

Procedure

HCl/diethyl ether (30.8 ml) was added to a solution of 4-amino-4'-chlorobenzophenone (35 g) in ethanol (250 ml) at room temperature and the mixture was stirred for 15 minutes. FeCl3.6H2O (69.4 g) and then ZnCl2 (2.05 g) were added portionwise and the mixture was stirred at 65° C. for 30 minutes. 3-Chloro-1-phenyl-1-propanone (25.46 g) was added and the mixture was stirred and refluxed for one night. The mixture was poured into ice and extracted with DCM. The organic layer was washed with K2CO3 10%, dried (MgSO4), filtered off and evaporated. The residue was crystallized from ACN. The mother layers were purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 99/1). The pure fractions were collected and evaporated, yielding 19.4 g (37%) of (4-chlorophenyl)(4-phenyl-6-quinolinyl)methanone (interm. 8-a).

Workup

  1. stirringthe mixture was stirred at 65° C. for 30 minutes
  2. stirringthe mixture was stirred
  3. temperaturerefluxed for one night
  4. additionThe mixture was poured into ice
  5. extractionextracted with DCM
  6. washThe organic layer was washed with K2CO3 10%
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered off
  9. customevaporated
  10. customThe residue was crystallized from ACN
  11. customThe mother layers were purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 99/1)
  12. customThe pure fractions were collected
  13. customevaporated

Sources & evidence

ORD record
ord-1a013dd4e43040f4b6d6f4c44f2ee8f9
Source dataset
uspto-grants-1999_10
Patent number
US05968952

Reaction notes

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