Sodium Hydroxide → Isopropyl 4-(3-chloro-2-thienyl)-2-methyl-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]-pyridine-3-carboxylate

HRID 329937Notes

Reaction equation

HRID 329937 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=O.[NH2:9]/[C:10](/[CH3:18])=[CH:11]\[C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13].[OH-:19].[Na+]>CCO.Cl>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[C:11]([C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])=[C:10]([CH3:18])[NH:9][C:10]2[CH2:18][O:19][C:12](=[O:13])[C:11]1=2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 27358253-Chlorothiophene-2-carbaldehydeHCID 111372742-Butenoic acid, 3-amino-, 1-methylethyl ester

Product 1

HCID 13853275Isopropyl 4-(3-chloro-2-thienyl)-2-methyl-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]-pyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

40 mmol of 3-chloro-thiophene-2-carbaldehyde, 40 mmol of 3-acetoxyacetoacetic acid ester and 40 mmol of isopropyl 3-aminocrotonate are boiled under reflux over NaOH in EtOH, alcoholic hydrochloric acid is then added and the mixture is boiled for 1 hour. It is concentrated and the residue is crystallized.

Workup

  1. additionis then added
  2. concentrationIt is concentrated
  3. customthe residue is crystallized

Sources & evidence

ORD record
ord-aee42490354240fa80b740a939dfb9d0
Source dataset
uspto-grants-1990_01
Patent number
US04894378

Reaction notes

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