Sodium Hydroxide → 7-Ethyl-2-methyl-4-oxo-4,7-dihydrothieno(2,3-b)pyridine-5-carboxylic acid

HRID 1679124Notes

Reaction equation

[CH2:1]([N:3]1[CH:8]=[C:7]([C:9]([O:11]CC)=[O:10])[C:6](=[O:14])[C:5]2[CH:15]=[C:16]([CH3:18])[S:17][C:4]1=2)[CH3:2].[OH-].[Na+]>C(O)(=O)C>[CH2:1]([N:3]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[C:6](=[O:14])[C:5]2[CH:15]=[C:16]([CH3:18])[S:17][C:4]1=2)[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 0.24 part of ethyl 7-ethyl-4,7-dihydro-2-methyl-4-oxothieno(2,3-b)pyridine-5-carboxylate and 3 parts by volume of 2N sodium hydroxide is heated at 90° C for 5 minutes. After cooling the solution is neutralized with acetic acid to give a precipitate which is collected by filtration, whereby 7-ethyl-4,7-dihydro-2-methyl-4-oxothieno(2,3-b)pyridine-5-carboxylic acid is obtained as crystals. Recrystallization from chloroform-ethanol gives colorless prisms melting at 232°-233° C. This product is identical with the product in Example 13.

Workup

temperatureAfter cooling the solution
customto give a precipitate which
filtrationis collected by filtration

Sources & evidence

ORD record: ord-bf6b8173d69c49db823d09cf7baa89c0
Source dataset: uspto-grants-1978_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04079060

Reaction notes

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