Hydrochloric Acid → HCID 19787178, compound

HRID 1885204Notes

Reaction equation

HRID 1885204 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:23]=[C:22]([CH2:24][CH3:25])[S:21][C:10]=2[N:11]([CH3:20])[C:12](=[O:19])[C:13]=1[C:14]([O:16]CC)=[O:15].[OH-].[K+].C(O)C.Cl>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:23]=[C:22]([CH2:24][CH3:25])[S:21][C:10]=2[N:11]([CH3:20])[C:12](=[O:19])[C:13]=1[C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 19787204HCID 19787204, compound

Product 1

HCID 19787178HCID 19787178, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 4-(2-chlorophenyl)-6,7-dihydro-2-ethyl-7-methyl-6-oxothieno[2,3-b]pyridine-5-carboxylate (1.10 g), KOH (0.49 g) and 80% ethanol (10 ml) was heated at 80° C. for 20 minutes and water was added. Then, the mixture was made acidic with 2N HCl and extracted with ethyl acetate. The extract was washed with water and dried over MgSO4, and then the solvent was distilled off. To the residue was added hexane to obtain 4-(2-chlorophenyl)-6,7-dihydro-2-ethyl-7-methyl-6-oxothieno[2,3-b]pyridine-5-carboxylic acid as crystals (0.91 g, 89.3%). The crystals were recrystallized from ethanol to obtain colorless prisms, mp: 155°-156° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over MgSO4
  4. distillationthe solvent was distilled off
  5. additionTo the residue was added hexane

Sources & evidence

ORD record
ord-df15af672ce349689c36c5583f4f0dc9
Source dataset
uspto-grants-1992_09
Patent number
US05143919

Reaction notes

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