4-Chlorobenzoic Acid → HCID 15524329, compound

HRID 1582196Notes

Reaction equation

HRID 1582196 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10](=[O:18])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1>>[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[NH:11][C:10](=[O:18])[CH2:9][CH:8]3[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[O:25])=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 63184-Chlorobenzoic AcidHCID 155243284-(3-Chlorophenyl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 15524329HCID 15524329, compoundYield 2.4%

Procedure

Intermnediate (1-a) (58.6 g), 4-chlorobenzoic acid (71.2 g) and polyphosphoric acid (580 g) were stirred at 140° C. for 48 hours. The mixture was poured into ice water and filtered off. The precipitate was washed with water, then with a diluted NH4OH solution and taken up in DCM. The organic layer was dried, filtered off and evaporated. The residue was purified by column chromatography over silica gel (eluent:CH2Cl2/CH3OH/NH4OH 99/1/0.1). The pure fractions were collected and evaporated, and recrystallized from CH2Cl2/CH3OH/DIPE, yielding 2.2 g of (±)-6-(4-chlorobenzoyl)-4-(3-chlorophenyl)-3,4-dihydro-2(1H)-quinolinone (interm. 1-b, mp. 194.8° C.).

Workup

  1. filtrationfiltered off
  2. washThe precipitate was washed with water
  3. customThe organic layer was dried
  4. filtrationfiltered off
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent:CH2Cl2/CH3OH/NH4OH 99/1/0.1)
  7. customThe pure fractions were collected
  8. customevaporated
  9. customrecrystallized from CH2Cl2/CH3OH/DIPE

Sources & evidence

ORD record
ord-ca307f1cc1d14af89b8f64f3b5915e23
Source dataset
uspto-grants-2004_05
Patent number
US06734194B2

Reaction notes

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