Hydrochloric Acid → HCID 59729933, compound

HRID 492623Notes

Reaction equation

HRID 492623 reaction equation
C([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]=[O:19])=[CH:14][CH:13]=2)=[N:7][CH:6]=1)C.CO.[OH-].[Na+].Cl>C(OCC)(=O)C.C1COCC1>[CH:18]([C:15]1[CH:16]=[CH:17][C:12]([O:11][C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:20])=[O:3])=[CH:6][N:7]=2)=[CH:13][CH:14]=1)=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 59730157HCID 59730157, compound

Product 1

HCID 59729933HCID 59729933, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 6-(4-Formyl-phenoxy)-nicotinic acid ethyl ester (1.5 g, 5.53 mmol), MeOH (5 mL), THF (5 mL), and 5N NaOH (aq) (2 mL). Reflux the reaction 18 hours and then add 1N HCl (aq) (2 mL). After concentrating the reaction on the rotovap, add Ethyl acetate to precipitate out the desired product. Filter and concentrate the ethyl acetate filtrate to afford 1.14 g (85% yield) of the title compound: TLC 1:1Hexanes:Ethyl acetate Rf:=0.01.

Workup

  1. temperatureReflux
  2. customthe reaction 18 hours
  3. concentrationAfter concentrating
  4. customthe reaction on the rotovap
  5. customto precipitate out the desired product
  6. filtrationFilter
  7. concentrationconcentrate the ethyl acetate filtrate

Sources & evidence

ORD record
ord-cd5df203931043dfba5c604939ec7401
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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