HCID 18957055, compound → HCID 15640829, compound

HRID 256688Notes

Reaction equation

HRID 256688 reaction equation
[O:1]=[C:2]1[N:7]2[N:8]=[CH:9][C:10]3[CH:14]=[CH:13][S:12][C:11]=3[C:6]2=[C:5]([C:15]([OH:17])=[O:16])[CH:4]=[C:3]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[OH-].[K+]>[C:9]([C:10]1[CH:14]=[CH:13][S:12][C:11]=1[C:6]1[NH:7][C:2](=[O:1])[C:3]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:4][C:5]=1[C:15]([OH:17])=[O:16])#[N:8]

Participants

3

Reactant 1

HCID 18957055HCID 18957055, compound

Product 1

HCID 15640829HCID 15640829, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

48.7 g of 7-oxo-8-phenyl-7H-pyrido[1,2-b]thieno[2,3-d]-pyridazine-10-carboxylic acid were added to a methanolic potassium hydroxide solution (prepared from 72 g of potassium hydroxide and 640 ml of methanol) and the mixture was heated to boiling under reflux for about 24 hours. The reaction mixture was evaporated to half in a vacuum, treated with 80 ml of water and adjusted to pH 1 by the addition of 1N hydrochloric acid. The separated crystals were filtered off under suction, washed with water and dried in a vacuum. There was obtained 48.6 g of 2-(3-cyano-2-thienyl)-1,6-dihydro-6-oxo-5-phenylnicotinic acid as yellow crystals with a m.p. of 255°-257° (methanol/N,N-dimethylformamide).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for about 24 hours
  3. customThe reaction mixture was evaporated to half in a vacuum
  4. additiontreated with 80 ml of water
  5. additionadjusted to pH 1 by the addition of 1N hydrochloric acid
  6. filtrationThe separated crystals were filtered off under suction
  7. washwashed with water
  8. customdried in a vacuum

Sources & evidence

ORD record
ord-3bdc0f07aeb847f4ad52ae188b584d94
Source dataset
uspto-grants-1993_11
Patent number
US05258387

Reaction notes

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