Cyclohexylamine → 3-Quinolinecarboxamide, 1,2-dihydro-N-cyclohexyl-4-hydroxy-2-oxo-

HRID 970626Notes

Reaction equation

HRID 970626 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:10][C:11]([C:13]1[C:14](=[O:24])[NH:15][C:16]2[C:21]([C:22]=1[OH:23])=[CH:20][CH:19]=[CH:18][CH:17]=2)=O)C>C1(C)C=CC=CC=1.O>[CH:1]1([NH:7][C:11]([C:13]2[C:14](=[O:24])[NH:15][C:16]3[C:21]([C:22]=2[OH:23])=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 7965CyclohexylamineHCID 54684458Ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate

Product 1

HCID 546801053-Quinolinecarboxamide, 1,2-dihydro-N-cyclohexyl-4-hydroxy-2-oxo-Yield 87.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Cyclohexylamine (13.88 mL, 121.33 mmol) was added to a solution of Compound 112 (9.4 g, 40.44 mmol) in toluene (200 mL) and refluxed for 4 h. The solution was cooled and the solvent was evaporated under vacuum. The residue obtained was suspended in water, briefly sonicated, and filtered. The crude product was recrystallized by ether to yield 10.1 g (87%) of white solids. M.P. 223° C. 1H NMR (DMSO-d6): δ 1.3 (m, 4H), 1.6 (m, 2H), 1.7 (m, 2H), 1.9 (m, 2H), 3.8 (m, 1H), 7.25 (t, J=7.7 Hz, 1H), 7.35 (d, J=8.3 Hz, 1H), 7.65 (t, J=7.2 Hz, 1H), 7.95 (d, J=7.7 Hz, 1H), 10.44 (b, 1H); EIMS (neg. mode): 285 (M−H).

Workup

  1. temperaturerefluxed for 4 h
  2. temperatureThe solution was cooled
  3. customthe solvent was evaporated under vacuum
  4. customThe residue obtained
  5. custombriefly sonicated
  6. filtrationfiltered
  7. customThe crude product was recrystallized by ether

Sources & evidence

ORD record
ord-52369b6dff47497b86e3306705244287
Source dataset
uspto-grants-2007_12
Patent number
US07312221B2

Reaction notes

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