Hydrochloric Acid → 2-(4-Methylpyridin-2-yl)-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one

HRID 889303Notes

Reaction equation

HRID 889303 reaction equation
C(O[C:4](=[O:14])[C:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[CH:6]O)C.[NH:15]([C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][N:18]=1)[NH2:16].C([O-])C.[Na+].Cl>C(O)C>[CH3:23][C:21]1[CH:20]=[CH:19][N:18]=[C:17]([N:15]2[C:4](=[O:14])[C:5]([C:8]3[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=3)=[CH:6][NH:16]2)[CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 122667392-Hydrazinyl-4-methylpyridineHCID 687080883-Hydroxy-2-pyridin-3-yl-acrylic acid ethyl ester

Product 1

HCID 591869542-(4-Methylpyridin-2-yl)-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.53 g (7.90 mmol) of the compound from Example 2A and 2.92 g (23.7 mmol) of the compound from Example 1A are dissolved 2 ml anhydrous ethanol under argon and the mixture is stirred at RT for 16 h. 537 g (7.90 mmol) sodium ethanolate are added, the reaction solution becoming dark red in color. The mixture is subsequently stirred at RT for 30 min and 7.9 ml 1 M hydrochloric acid are then added. The solution is partly concentrated, a precipitate separating out. This is filtered off, washed with water (twice with 5 ml each time) and with MTBE (5 ml) and dried in vacuo. 435 mg (22% of th.) of the title compound are obtained.

Workup

  1. stirringThe mixture is subsequently stirred at RT for 30 min
  2. concentrationThe solution is partly concentrated
  3. customa precipitate separating out
  4. filtrationThis is filtered off
  5. washwashed with water (twice with 5 ml each time) and with MTBE (5 ml)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-63bf55f4b9034805bcbdb450d41003c6
Source dataset
uspto-grants-2012_08
Patent number
US08252817B2

Reaction notes

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