4-Nitrobenzoic Acid → HCID 21082091, compound

HRID 346971Notes

Reaction equation

HRID 346971 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.[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20].[NH4+].[OH-]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:26](=[O:27])[C:25]4[CH:24]=[CH:23][C:22]([N+:19]([O-:21])=[O:20])=[CH:30][CH:29]=4)[CH:16]=3)[NH:11][C:10](=[O:18])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 61084-Nitrobenzoic AcidHCID 14923Ammonium HydroxideHCID 155243284-(3-Chlorophenyl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 21082091HCID 21082091, compoundYield 27%

Conditions

Temperature
140 °C

Procedure

(±)-4-(3-chlorophenyl)-3,4-dihydro-2(1H)-quinolinone (described in WO 97/21701) (0.0776 mol), then 4-nitro-benzoic acid (0.233 mol) were added at 100° C. to polyphosphoric acid (200 g). The mixture was stirred at 140° C. for 72 hours, cooled at 80° C., poured out into ice water, basified with NH4OH (concentrated) and extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue (19.4 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2; 15–35 μm). One fraction was collected and the solvent was evaporated. The residue (9.1 g) was crystallized from 2-propanone. The precipitate was filtered off and dried, yielding 8.5 g (27%) of (±)-4-(3-chlorophenyl)-3,4-dihydro-6-(4-nitrobenzoyl)-2(1H)-quinolinone, mp. 147° C. (intermediate 15).

Workup

  1. temperaturecooled at 80° C.
  2. extractionextracted with CH2Cl2
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue (19.4 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2; 15–35 μm)
  8. customOne fraction was collected
  9. customthe solvent was evaporated
  10. customThe residue (9.1 g) was crystallized from 2-propanone
  11. filtrationThe precipitate was filtered off
  12. customdried

Sources & evidence

ORD record
ord-85453771f9e947db84551e4096cdb84d
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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