Hydrochloric Acid → 3-formyl-2-heptyl-4(1H)-quinolone

HRID 2222389Notes

Reaction equation

HRID 2222389 reaction equation
[CH2:1]([C:8]1[NH:9][C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C1N2CN3CN(C2)CN1C3.[C:29](O)(C(F)(F)F)=[O:30].Cl>O.CO>[CH:29]([C:17]1[C:16](=[O:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 164974MY 12-62c

Product 1

HCID 99001373-formyl-2-heptyl-4(1H)-quinoloneYield 40%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-heptyl-4(1H)-quinolone (5 mmol), hexamine (2.5 mmol), and TFA (7.5 ml) was stirred at reflux under nitrogen for 30 hours. MeOH (15 ml) and water (15 ml) were added, and heating was continued for 1 hour. 3 M HCl (5 ml) was added and the heating was continued for a further period of 30 minutes. The mixture was cooled and the precipitate removed by filtration and washed with water. The solid on trituration with acetone afforded the title compound in 40% yield. Recrystallisation from MeOH/EtOAc gave colourless needles, mp 245-248° C. (dec).

Workup

  1. temperatureat reflux under nitrogen for 30 hours
  2. temperatureheating
  3. waitthe heating was continued for a further period of 30 minutes
  4. temperatureThe mixture was cooled
  5. customthe precipitate removed by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-30eb70bd62794f529bd29aa891bda92e
Source dataset
uspto-grants-2008_05
Patent number
US07371779B2

Reaction notes

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