HCID 57456934, compound → 4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

HRID 711665Notes

Reaction equation

HRID 711665 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13]([O:15]CC1C=CC=CC=1)=[O:14]>CN(C=O)C.[Pd]>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13]([OH:15])=[O:14]

Participants

4

Reactant 1

HCID 57456934HCID 57456934, compound

Product 1

HCID 5948214-amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acidYield 12%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Benzyl 4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate (Example 66a) (0.6 g, 2.04 mmol) was dissolved in DMF (8 mL) and heated at 70° C. under a hydrogen balloon in the presence of 10% Pd/C (0.15 g) for 1 hour. The Pd/C was filtered out and washed with dichloromethane and the solvents were removed under vacuum. The residue was dissolved/suspended in NaOH (2M, 40 mL), stirred at room temperature for 30 minutes and the solution washed with dischloromethane. The aqueous layer was cooled to 0° C. and acidified to pH 1 with 2M HCl. The resultant precipitate was collected and washed with dichloromethane to give 4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (0.050 g, 12%) as a light yellow solid. M.p.: >250° C. 1H NMR (400 MHz, DMSO-d6) δ 7.32 (m, 1H), 7.39 (d, J=7.6 Hz, 1H), 7.69 (m, 1H), 8.27 (d, J=8.4 Hz, 1H), 8.86 (s, 1H), 9.87 (s, 1H), 11.95 (s, 1H). MS 205 (MH+).

Workup

  1. filtrationThe Pd/C was filtered out
  2. washwashed with dichloromethane
  3. customthe solvents were removed under vacuum
  4. washthe solution washed with dischloromethane
  5. temperatureThe aqueous layer was cooled to 0° C.
  6. customThe resultant precipitate was collected
  7. washwashed with dichloromethane

Sources & evidence

ORD record
ord-8afe3cd0ea49481db5aea9ec449129eb
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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