Potassium Hydroxide → HCID 18957052, compound

HRID 1885356Notes

Reaction equation

HRID 1885356 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]1=[C:12]([C:23]([O:25]C)=[O:24])[CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:16])[N:9]1[N:8]=[CH:7]2.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([C:7]#[N:8])[C:11]=1[C:10]1[NH:9][C:15](=[O:16])[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][C:12]=1[C:23]([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18957075HCID 18957075, compound

Product 1

HCID 18957052HCID 18957052, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A.a) A mixture of 72.9 g of methyl 11-chloro-4-oxo-3-phenyl-4H-pyrido[2,1-a]phthalazine-1-carboxylate, 112 g of potassium hydroxide and 1200 ml of methanol was heated to boiling under reflux for 46 hours under argon. The mixture was then concentrated to about 200 ml, the yellow suspension was diluted with 1000 ml of water, filtered and the aqueous phase was extracted three times with 200 ml of methylene chloride each time. The aqueous phase was acidified with 25 percent hydrochloric acid and the separated crystals were filtered off, washed with water and dried in a vacuum. There was obtained 69.7 g of 2-[2-chloro-6-cyanophenyl]-1,6-dihydro-6-oxo-5-phenylnicotinic acid as yellowish crystals with a m.p. of 279°-281° (decomposition).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 46 hours under argon
  3. concentrationThe mixture was then concentrated to about 200 ml
  4. additionthe yellow suspension was diluted with 1000 ml of water
  5. filtrationfiltered
  6. extractionthe aqueous phase was extracted three times with 200 ml of methylene chloride each time
  7. filtrationthe separated crystals were filtered off
  8. washwashed with water
  9. customdried in a vacuum

Sources & evidence

ORD record
ord-6934da84eecb42d38667ae82a29ef85b
Source dataset
uspto-grants-1992_09
Patent number
US05143912

Reaction notes

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