Acetohydrazide → acetic acid [2-(1-pyridin-3-yl-1H-pyrazol-4-yl)-6,7-dihydro-5H-quinolin-ylidene]-hydrazide

HRID 1478534Notes

Reaction equation

HRID 1478534 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12]3[CH:21]=[CH:20][C:19]4[CH2:18][CH2:17][CH2:16][C:15](=O)[C:14]=4[N:13]=3)[CH:9]=[N:8]2)[CH:2]=1.[C:23]([NH:26][NH2:27])(=[O:25])[CH3:24]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12]3[CH:21]=[CH:20][C:19]4[C:18](=[N:27][NH:26][C:23](=[O:25])[CH3:24])[CH2:17][CH2:16][CH2:15][C:14]=4[N:13]=3)[CH:9]=[N:8]2)[CH:2]=1

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 900442112-[1-(3-pyridyl)pyrazol-4-yl]-6,7-dihydro-5H-quinolin-8-one

Product 1

HCID 131736508acetic acid [2-(1-pyridin-3-yl-1H-pyrazol-4-yl)-6,7-dihydro-5H-quinolin-ylidene]-hydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(1-pyridin-3-yl-1H-pyrazol-4-yl)-6,7-dihydro-5H-quinolin-8-one (125 mg, 0.43 mmol) and acetic acid hydrazide (47 mg, 0.63 mmol) in ethanol (5 ml) was heated at 75° C. overnight. The reaction mixture was evaporated to dryness, the residue was taken up in ethyl acetate and washed twice with water. The organic phase was dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by flash chromatography eluting with ethyl acetate/methanol 19:1 gave the title product as white solid.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. washwashed twice with water
  3. dry with materialThe organic phase was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography
  7. washeluting with ethyl acetate/methanol 19:1

Sources & evidence

ORD record
ord-5756cb175f1841de9ece62c4912a99e9
Source dataset
uspto-grants-2016_08
Patent number
US09403845B2

Reaction notes

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