Hydrochloric Acid → HCID 178498606, compound

HRID 496559Notes

Reaction equation

HRID 496559 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:20])=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:8]([C:12]([O:14]C)=[O:13])=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O>[C:16]([C:7]1[C:8]([C:12]([OH:14])=[O:13])=[N:9][C:10]2[C:5]([C:6]=1[OH:20])=[CH:4][CH:3]=[C:2]([Cl:1])[CH:11]=2)([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178418477HCID 178418477, compound

Product 1

HCID 178498606HCID 178498606, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred suspension of dimethyl 7-chloro-4-hydroxyquinoline-2,3-dicarboxylate (1.0 g, 3.38 mmol) in water (20 mL) was added an aqueous solution of sodium hydroxide (0.27 g, 6.75 mmol). Upon addition, the suspension dissolved. The reaction mixture was warmed to 60° C. for 1 hour. After this time the reaction was cooled to room temperature and acidified with concentrated hydrochloric acid. The product was then extracted into diethyl ether and ethyl acetate. The organic extracts were dried over MgSO4, filtered and concentrated in vacuo to provide the title compound as a solid (900 mg). This material was purified by recrystallization employing an ethyl acetate/hexane co-solvent system to provide the title compound (571 mg, 60%) as a white solid mp 296° C. (dec); MS (CI)=238 (M+H). Analysis for C12H8NO5Cl.0.45 CH3CO2CH2CH3.0.10 H2O: Calc'd: C, 51.30; H, 3.68; N, 4.34, Found: C, 51.28; H, 3.62; N, 3.97;1H NMR 8.22 (d, J=8.7 Hz, 1H), 7.92 (d, J=1.8 Hz, 1H), 7.28 (dd, J=8.7, 1.8 Hz, 1H), 3.90 (s, 3H).

Workup

  1. additionUpon addition
  2. dissolutionthe suspension dissolved
  3. temperatureAfter this time the reaction was cooled to room temperature
  4. extractionThe product was then extracted into diethyl ether and ethyl acetate
  5. dry with materialThe organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-80292136ff344c8c94194082a712a03a
Source dataset
uspto-grants-2005_09
Patent number
US06946463B2

Reaction notes

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