Acetic Acid → HCID 19867718, compound

HRID 1198930Notes

Reaction equation

HRID 1198930 reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[C:7]([CH3:20])[CH:8]=[C:9]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[NH2:19])[CH:10]=2)[NH:5][C:4](=[O:21])[CH2:3]1.[C:22](O)(=O)[CH3:23]>>[CH3:1][CH:2]1[C:11]2[C:6](=[C:7]([CH3:20])[CH:8]=[C:9]([N:12]3[C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[N:19]=[C:22]3[CH3:23])[CH:10]=2)[NH:5][C:4](=[O:21])[CH2:3]1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 19867712HCID 19867712, compound

Product 1

HCID 19867718HCID 19867718, compound

Procedure

3,4-Dihydro-4,8-dimethyl-6-[(N-2-aminophenyl)-amino]-2-(1H)-quinolone (0.39 g) was added with stirring to glacial acetic acid (3 cm3) and the mixture heated under reflux for 5 hours. Solvent was evaporated in vacuo and the residue partitioned between saturated sodium carbonate solution (40 cm3) and dichloromethane (50 cm3). The aqueous phase was separated and re-extracted with dichloromethane (2×50 cm3) and the combined and dried (MgSO4) organic extracts were evaporated in vacuo to give a solid which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]). Elution with methanol:chloroform, 1:100 by volume followed by combination and evaporation at appropriate fractions gave a solid which was triturated with diethyl ether to afford the title compound, m.p. 248°-252°, (0.11 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 5 hours
  3. customSolvent was evaporated in vacuo
  4. customthe residue partitioned between saturated sodium carbonate solution (40 cm3) and dichloromethane (50 cm3)
  5. customThe aqueous phase was separated
  6. extractionre-extracted with dichloromethane (2×50 cm3)
  7. dry with materialdried (MgSO4) organic extracts
  8. customwere evaporated in vacuo
  9. customto give a solid which
  10. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  11. washElution with methanol
  12. customchloroform, 1:100 by volume followed by combination and evaporation at appropriate fractions
  13. customgave a solid which
  14. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-c36cf02767f648a29ef749972bc90f79
Source dataset
uspto-grants-1990_02
Patent number
US04898872

Reaction notes

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