Ethanol → HCID 12428607, compound

HRID 1973419Notes

Reaction equation

HRID 1973419 reaction equation
[OH:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][N:5]=[C:4]2[S:13][C:14]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:3]=12.[OH-].[K+].[CH2:22](O)[CH3:23].C(I)C>O>[CH2:22]([N:5]1[CH:6]=[C:7]([C:8]([OH:10])=[O:9])[C:2](=[O:1])[C:3]2[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[S:13][C:4]1=2)[CH3:23]

Participants

6

Reactant 4

HCID 702EthanolHCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 178469712HCID 178469712, compound

Product 1

HCID 12428607HCID 12428607, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.38 parts of ethyl 4-hydroxy-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridine-3-carboxylate, 11 parts by volume of 10 percent aqueous potassium hydroxide, 44 parts by volume of ethanol and 45 parts by volume of water and 1.5 parts by volume of ethyl iodide is refluxed for 4 hours and the product is isolated in a manner similar to that described in Example 13, whereby 1-ethyl-1,4,5,6,7,8-hexahydro-4-oxo[1]benzothieno[2,3-b]pyridine-3-carboxylic acid is obtained as crystals. Recrystallization from ethanol and, then, from tetrahydrofuran gives colorless needles melting at 218°-221° C.

Workup

  1. temperatureis refluxed for 4 hours
  2. customthe product is isolated in a manner similar to

Sources & evidence

ORD record
ord-60a4c8b767c547efa676ef969e9731c8
Source dataset
uspto-grants-1976_12
Patent number
US03997545

Reaction notes

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