Hydrochloric Acid → HCID 59699551, compound

HRID 901238Notes

Reaction equation

HRID 901238 reaction equation
[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[CH3:14][O:15][C:16]1[CH:34]=[CH:33][C:19]([CH2:20][N:21]2[C:26]3[N:27]=[CH:28][CH:29]=[CH:30][C:25]=3[C:24](=O)[O:23]C2=O)=[CH:18][CH:17]=1.Cl>CC(N(C)C)=O>[CH2:6]([O:5][C:3]([C:2]1[C:1](=[O:9])[N:21]([CH2:20][C:19]2[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[CH:34][CH:33]=2)[C:26]2[C:25]([C:24]=1[OH:23])=[CH:30][CH:29]=[CH:28][N:27]=2)=[O:4])[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 59699561HCID 59699561, compound

Product 1

HCID 59699551HCID 59699551, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Diethyl malonate (2.37 mL, 15.61 mmol) was added slowly to a suspension of NaH (60% in mineral oil, 0.62 g, 15.61 mmol) in dimethylacetamide (40 mL) and stirred at room temperature for 0.5 h under inert atmosphere. 1-(4-Methoxy-benzyl)-1H-pyrido[2,3-d][1,3]oxazine-2,4-dione (12) (4.47 g, 15.61 mmol) was added to the solution and heated at 110° C. for 3 h (TLC control). The solution was cooled and poured into ice water. The pH of the solution was adjusted to 3 by cold 10% HCl. The solids formed were filtered, washed by excess water, and dried in a vacuum oven. The crude product was recrystallized by ethylacetate to yield 1.2 g (21%) of 4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (13) as white solids. MP: 153° C.; 1H-NMR (DMSO-d6): δ 1.31 (t, J=7.0 Hz, 3H), 3.68 (s, 3H), 4.32 (q, J=7.0 Hz, 2H), 5.47 (s, 2H), 6.81 (d, J=7.7 Hz, 2H), 7.21 (d, J=7.6 Hz, 2H), 7.36 (d, J=7.6 Hz, 1H), 8.42 (dd, J=1.5, 7.5 Hz, 1H), 8.73 (dd, J=1.5, 7.5 Hz, 1H), 13.00 (S, 1H); EIMS: 355 (M+1).

Workup

  1. temperatureheated at 110° C. for 3 h (TLC control)
  2. temperatureThe solution was cooled
  3. customThe solids formed
  4. filtrationwere filtered
  5. washwashed by excess water
  6. customdried in a vacuum oven
  7. customThe crude product was recrystallized by ethylacetate

Sources & evidence

ORD record
ord-a8f46aa738714357b7beb92442861110
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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