HCID 67259967, compound → HCID 67259322, compound

HRID 907955Notes

Reaction equation

HRID 907955 reaction equation
[OH:1][C:2]1[C:11]2[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=[CH:7][C:6]=2[N:5](CC2C=CC(OC)=CC=2)[C:4](=[O:26])[C:3]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>FC(F)(F)C(O)=O>[OH:1][C:2]1[C:11]2[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=[CH:7][C:6]=2[NH:5][C:4](=[O:26])[C:3]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

3

Reactant 1

HCID 67259967HCID 67259967, compound

Product 1

HCID 67259322HCID 67259322, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of ethyl 4-hydroxy-1-(4-methoxybenzyl)-2-oxo-3-phenyl-1,2-dihydroquinoline-5-carboxylate (298 mg, 2 mmol) in trifluoroacetic acid was heated to reflux for 48 h. After the removal of the solvents, the residue was washed by ethyl acetate to obtain the title compound as a white solid (250 mg, yield 32%). LC-MS (ESI) m/z: 310 (M+1)+. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 1.25 (t, J=7.2 Hz, 3H), 4.23 (q, J=7.2 Hz, 2H), 7.08 (d, J=7.2 Hz, 1H), 7.31-7.43 (m, 6H), 7.52 (t, J=8 Hz, 1H), 10.39 (s, 1H), 11.64 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 h
  3. customAfter the removal of the solvents
  4. washthe residue was washed by ethyl acetate

Sources & evidence

ORD record
ord-0f43f74e5f834d09910f5f162d2f55a0
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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