Ethanol → HCID 12428607, compound

HRID 1605970Notes

Reaction equation

HRID 1605970 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 % 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. Recrytallization 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-6eb5b8aff02140328c45c5a375156924
Source dataset
uspto-grants-1976_04
Patent number
US03951989

Reaction notes

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