Hydrochloric Acid → Ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate

HRID 1371502Notes

Reaction equation

HRID 1371502 reaction equation
C([C:3](CC)([C:7]([O-:9])=[O:8])C([O-])=O)C.[H-].[Na+].[H][H].[C:16]12[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=1)[NH:21][C:20](=[O:27])[O:19][C:17]2=O.Cl.[CH3:29][C:30](N(C)C)=O>>[CH2:29]([O:9][C:7]([C:3]1[C:20](=[O:27])[NH:21][C:22]2[C:16]([C:17]=1[OH:19])=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:8])[CH3:30]

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 8359Isatoic AnhydrideHCID 24758Sodium hydrideHCID 31374Dimethylacetamide2×HCID 69515632,2-DiethylpropanedioateHCID 178418361HCID 178418361, compound

Product 1

HCID 54684458Ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylateYield 47%

Conditions

Temperature
90 °C

Procedure

A solution of diethylmalonate (80 g, 0.50 mol) was added slowly to a suspension of sodium hydride (60% in mineral oil, 22 g, 0.55 mol) in dimethylacetamide under N2 atmosphere. The mixture was allowed to stir at room temperature until the evolution of hydrogen gas ceased, then heated to 90° C. for 30 min. and cooled to room temperature. A solution of isatoic anhydride (89.72 g, 0.55 mmol) in dimethylacetamide was added slowly and heated at 120° C. for 15 h. The mixture was cooled to room temperature, poured into ice water and acidified by cold 10% HCl. The solids formed were filtered and washed several times by water to yield 55 g (47%) of white solids. Mp 173° C. 1H NMR (DMSO-d6): δ 1.30 (t, J=6.9 Hz, 3H), 4.33 (q, J=6.9 Hz, 2H), 7.18 (t, J=7.5 Hz, 1H), 7.26 (d, J=8.2 Hz, 1H), 7.62 (t, J=7.2 Hz, 1H), 7.93 (d, J=8.0 Hz, 1H) 11.50 (s, 1H), 13.5 (s, 1H). EIMS m/z 234 (M+1), 256 (M+23). Anal. (C12H11NO4) C, H, N.

Workup

  1. temperaturecooled to room temperature
  2. temperatureheated at 120° C. for 15 h
  3. temperatureThe mixture was cooled to room temperature
  4. customThe solids formed
  5. filtrationwere filtered
  6. washwashed several times by water

Sources & evidence

ORD record
ord-8abc640c19f9414fa7a13c67b66e98b3
Source dataset
uspto-grants-2007_01
Patent number
US07157469B2

Reaction notes

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