Hydrochloric Acid → HCID 89585074, compound

HRID 1500963Notes

Reaction equation

HRID 1500963 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[CH:4][N:3]1[CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13].O.[OH-].[Li+].O1CCCC1.Cl>O.CO>[O:1]=[C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][N:3]1[CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 89581114HCID 89581114, compound

Product 1

HCID 89585074HCID 89585074, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of methyl 2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylate (90 mg, 0.35 mmol), lithium hydroxide monohydrate (57.1 mg, 1.36 mmol), tetrahydrofuran (5 mL), methanol (1 mL) and water (1 mL) was stirred at 20° C. for 4 hours. The mixture was neutralized to pH=1 with concentrated hydrochloric acid and then extracted with acetic ether (15 mL×3). The combined organic phase was dried by sodium sulfate, then filtered. The filtrate was concentrated in vacuum to give 2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylic acid as a white solid (60 mg, 70%). LRMS (M+H)− m/z: cald. 243.09. found 243.

Workup

  1. extractionextracted with acetic ether (15 mL×3)
  2. dry with materialThe combined organic phase was dried by sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuum

Sources & evidence

ORD record
ord-64ea9fd264b143619821a18f311d63c1
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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