HCID 67097724, compound → Methyl 4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate

HRID 44398Notes

Reaction equation

HRID 44398 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11](=[O:19])[C:10]=2[C:20]([O:22][CH3:23])=[O:21])=CC=1>C(O)(C(F)(F)F)=O>[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11](=[O:19])[C:10]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

3

Reactant 1

HCID 67097724HCID 67097724, compound

Product 1

HCID 658173Methyl 4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylateYield 42.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Methyl 4-(4-methoxybenzylamino)-2-oxo-1,2-dihydroquinoline-3-carboxylate (Example 68a) (0.841 g, 2.49 mmol) was dissolved in TFA (5 mL) and stirred at room temperature for 30 minutes. The TFA was removed under reduced pressure, and the residue was dissolved in dichloromethane, then precipitated out by adding excess diethyl ether. The resultant solid was collected by filtration, suspended in dichloromethane, and washed with concentrated sodium bicarbonate. The solid was collected to give methyl 4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate (0.230 g, 42%) as a white solid. M.p.: 236° C. 1H NMR (400 MHz, DMSO-d6) δ3.73 (s, 3H), 7.12 (t, J=8.0 Hz, 1H), 7.17 (d, J=8.0 Hz, 1H), 7.52 (t, J=8.0 Hz, 1H), 8.08 (d, J=8.0 Hz, 1H), 8.38 (bs, 2H), 10.88 (bs, 1H). MS 219 (MH+).

Workup

  1. customThe TFA was removed under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. customprecipitated out
  4. additionby adding excess diethyl ether
  5. filtrationThe resultant solid was collected by filtration
  6. washwashed with concentrated sodium bicarbonate
  7. customThe solid was collected

Sources & evidence

ORD record
ord-8baaea6df5bb4c318efcc40347103c58
Source dataset
uspto-grants-2013_09
Patent number
US08541421B2

Reaction notes

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