Sodium Hydroxide → HCID 22266462, compound

HRID 416575Notes

Reaction equation

HRID 416575 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 ethyl acetate 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 ethyl acetate
  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-4e0cf7e0035843d4ac95e49024ca04b3
Source dataset
uspto-grants-2012_01
Patent number
US08088924B2

Reaction notes

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