4-Chlorobenzoic Acid → HCID 15524329, compound

HRID 564823Notes

Reaction equation

HRID 564823 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 (MgSO4), filtered off and evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH99/1/0.1). 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. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered off
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH99/1/0.1)
  7. customThe pure fractions were collected
  8. customevaporated
  9. customrecrystallized from CH2Cl2/CH3OH/DIPE

Sources & evidence

ORD record
ord-1bebb2a3c1644ae099806af8bd7a9753
Source dataset
uspto-grants-2001_01
Patent number
US06169096A

Reaction notes

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