Sodium Hydroxide → HCID 900921, compound

HRID 564757Notes

Reaction equation

HRID 564757 reaction equation
C([O:3][C:4]([C:6]1[C:11]([CH3:12])=[C:10]([C:13]#[N:14])[C:9](=[O:15])[N:8]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:7]=1)=[O:5])C.[OH-].[Na+]>C(O)C.O>[C:13]([C:10]1[C:9](=[O:15])[N:8]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:7]=[C:6]([C:4]([OH:5])=[O:3])[C:11]=1[CH3:12])#[N:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 687973HCID 687973, compound

Product 1

HCID 900921HCID 900921, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5-cyano-4-methyl-1-(4-methoxy-phenyl)-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid ethyl ester (15 g, 0.048 mol, prepared as described in example 23) in a mixture of ethanol (250 ml) and water (100 ml) was added sodium hydroxide (2.1 g, 0.053 mol). The reaction mixture was stirred at room temperature for 16 h, the volatiles were evaporated and the residue diluted with water (200 ml). The aqueous phase was washed with ethyl acetate (250 ml) and pH was adjusted to pH=2 by addition of concentrated hydrochloric acid. The precipitate was filtered off and washed with water (2×80 ml) and dried in vacuo at 50° C. for 16 h which afforded 12.3 g (90%) of 5-cyano-1-(4-methoxy-phenyl)-4-methyl-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid as a solid.

Workup

  1. customthe volatiles were evaporated
  2. additionthe residue diluted with water (200 ml)
  3. washThe aqueous phase was washed with ethyl acetate (250 ml) and pH
  4. additionwas adjusted to pH=2 by addition of concentrated hydrochloric acid
  5. filtrationThe precipitate was filtered off
  6. washwashed with water (2×80 ml)
  7. customdried in vacuo at 50° C. for 16 h which

Sources & evidence

ORD record
ord-1960bf005a24407c9594ba4d67163c73
Source dataset
uspto-grants-2001_01
Patent number
US06169087A

Reaction notes

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