4-Chlorobenzoic Acid → HCID 15524329, compound

HRID 852264Notes

Reaction equation

HRID 852264 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

Intermediate (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-10548ae231c940f68e6dfa995b1a8a6c
Source dataset
uspto-grants-2007_08
Patent number
US07253183B2

Reaction notes

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