Acetic Acid → HCID 59598355, compound

HRID 2266337Notes

Reaction equation

HRID 2266337 reaction equation
[C:1]([CH2:9][C:10]([O-:12])=O)(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:13][NH:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C>O>[CH3:13][N:14]1[C:1]([C:2]2[CH:3]=[CH:4][N:5]=[CH:6][CH:7]=2)=[CH:9][C:10](=[O:12])[N:15]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 101978131-methyl-2-phenylhydrazineHCID 17817801HCID 17817801, compound

Product 1

HCID 59598355HCID 59598355, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

thyl isonicotinoylacetate (3.01 g, 16 mmol) and 1-methyl-2-phenylhydrazine (2.03 g, 17 mmol) were suspended in water (50 ml) and glacial acetic acid (1.35 ml, 23 mmol) was added. The flask was fitted with a reflux condenser and placed in a preheated oil bath (115 C) and stirred. After 4 hours, the reaction cooled to room temperature and extracted with EtOAc (2×100 ml; 50 ml), 10:1 DCM/MeOH (110 ml), and EtOAc again. The organic phases were combined, dried over sodium sulfate, filtered, and concentrated. The crude material was purified on silica gel (DCM->20:1->10:1 DCM/MeOH->10:1->4:1 DCM/2 N ammonia in MeOH). Fractions with product collected, concentrated, and repurified on silica gel using DCM->20:1 DCM/MeOH->5:1 DCM/2 N ammonia in MeOH). The fractions with product were collected and concentrated to give 1-methyl-2-phenyl-5-(pyridin-4-yl)-1,2-dihydropyrazol-3-one (3.31 g, 70% purity, 9.2 mmol, 59%). MS (ESI pos. ion) m/z: 252 (MH+). Calc'd exact mass for C15H13N3O: 251.

Workup

  1. customThe flask was fitted with a reflux condenser
  2. customplaced in a preheated oil bath
  3. extractionextracted with EtOAc (2×100 ml; 50 ml), 10:1 DCM/MeOH (110 ml), and EtOAc again
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified on silica gel (DCM->20:1->10:1 DCM/MeOH->10:1->4:1 DCM/2 N ammonia in MeOH)
  8. customFractions with product collected
  9. concentrationconcentrated
  10. customrepurified on silica gel
  11. customThe fractions with product were collected
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-16b8ca6ae35544c0a75f1f4a117f6d39
Source dataset
uspto-grants-2010_12
Patent number
US07858623B2

Reaction notes

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