Hydrochloric Acid → 2-(1-(Benzyloxy)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetic acid

HRID 1054216Notes

Reaction equation

HRID 1054216 reaction equation
[CH2:1]([O:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([OH:19])=[C:11]([C:20]([NH:22][CH2:23][C:24]([O:26]CC)=[O:25])=[O:21])[C:10]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1.O>[CH2:1]([O:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([OH:19])=[C:11]([C:20]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21])[C:10]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 118451768Ethyl 2-(1-(benzyloxy)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate

Product 1

HCID 902693962-(1-(Benzyloxy)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetic acidYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirring solution of ethyl 2-(1-(benzyloxy)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (500 mg, 1.261 mmol) in THF (5 mL) was added solution of sodium hydroxide (126 mg, 3.15 mmol) in water (5 mL) and stirred at 25-30° C. for 2 h. Organic solvent was distilled out followed by addition of ice cold water. Reaction mixture was then acidified using dil. HCl up to pH-2-3. Precipitated solid was filtered to get titled compound in 80% yield.

Workup

  1. distillationOrganic solvent was distilled out
  2. additionfollowed by addition of ice cold water
  3. customReaction mixture
  4. customPrecipitated solid
  5. filtrationwas filtered

Sources & evidence

ORD record
ord-9a87e2525faf452cad4a6d552710da1a
Source dataset
uspto-grants-2016_07
Patent number
US09394300B2

Reaction notes

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