Water → HCID 59340053, compound

HRID 908576Notes

Reaction equation

HRID 908576 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:13])[C:5](=[O:14])[C:4]=1[C:15]([NH:17][CH2:18][C:19]([O:21]C)=[O:20])=[O:16].[OH-].[Na+].ClCCl.O>C1COCC1>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:13])[C:5](=[O:14])[C:4]=1[C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 67388388HCID 67388388, compound

Product 1

HCID 59340053HCID 59340053, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(4-methoxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (0.150 g, 0.5 mmol) was dissolved in THF in a 25 mL round bottom flask. NaOH was added and the mixture was stirred for 1.5 hours. Dichloromethane and water were added to the reaction and the layers were separated. The aqueous layer was washed two more times with dichloromethane. To the aqueous phase, IN HCL was added until the pH was approximately 1. The aqueous phase was then extracted with 25% IPA/CHCl3, dried with MgSO4 and concentrated on a roto-evaporator. The compound was then purified by HPLC to give the desired product as a white solid.

Workup

  1. customthe layers were separated
  2. washThe aqueous layer was washed two more times with dichloromethane
  3. additionTo the aqueous phase, IN HCL was added until the pH was approximately 1
  4. extractionThe aqueous phase was then extracted with 25% IPA/CHCl3
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated on a roto-evaporator
  7. customThe compound was then purified by HPLC

Sources & evidence

ORD record
ord-26023317804b4776ae0e1349be6ef805
Source dataset
uspto-grants-2011_09
Patent number
US08017626B2

Reaction notes

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