Sodium Hydroxide → HCID 22266462, compound

HRID 489284Notes

Reaction equation

HRID 489284 reaction equation
C[O:2][C:3]([C:5]1[C:18](=[O:19])[N:9]2[CH2:10][CH2:11][C:12]3[C:17]([C:8]2=[CH:7][CH:6]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:4].[OH-].[Na+]>O1CCOCC1>[O:19]=[C:18]1[N:9]2[CH2:10][CH2:11][C:12]3[C:17]([C:8]2=[CH:7][CH:6]=[C:5]1[C:3]([OH:4])=[O:2])=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10956146HCID 10956146, compound

Product 1

HCID 22266462HCID 22266462, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-oxo-6,7-dihydropyrido[2,1,a]isoquinoline-3-carboxylic acid methyl ester (3-101-02) (252 mg) in dioxane (2.0 mL) was 2 mol/L aqueous sodium hydroxide solution (2.0 mL) at room temperature. After the reaction mixture was stirred for 1 h, and washed with diethyl ether, adjusted to be acidic with conc. hydrochloric acid. To the reaction mixture were added water and ethyl acetate, and the organic layer was separated. The aqueous layer was extracted three times with ethylacetate and the combined organic layers were washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to give 4-oxo-6,7-dihydropyrido[2,1,a]isoquinoline-3-carboxylic acid (3-101-03) (209 mg, 88%) as a white solid.

Workup

  1. customat room temperature
  2. washwashed with diethyl ether
  3. additionTo the reaction mixture were added water and ethyl acetate
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted three times with ethylacetate
  6. washthe combined organic layers were washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4e490fcb4e5546aa859b21b3ace87391
Source dataset
uspto-grants-2005_12
Patent number
US06977266B2

Reaction notes

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