4-[(4-benzylphenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid → 7-Benzyl-1-methyl-1,4-dihydro-pyrazolo[4,3-b]quinolin-9-one

HRID 2119625Notes

Reaction equation

HRID 2119625 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[CH:16]=[N:17][N:18]([CH3:23])[C:19]=2[C:20]([OH:22])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>P(Cl)(Cl)(Cl)=O>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]2[NH:14][C:15]3[CH:16]=[N:17][N:18]([CH3:23])[C:19]=3[C:20](=[O:22])[C:12]=2[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 234423114-[(4-benzylphenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid

Product 1

HCID 98571507-Benzyl-1-methyl-1,4-dihydro-pyrazolo[4,3-b]quinolin-9-oneYield 84.4%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of 4-[(4-benzylphenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid (EXAMPLE 11, step 1, 4.86 g, 15.81 mmol) in phosphorus oxychloride (40 ml) was refluxed for 3 h. After cooling to room temperature, the mixture was concentrated and dried in vacuo. The mixture was dissolved in ethyl acetate (300 ml), washed with water (100 ml) and saturated aqueous sodium bicarbonate (100 ml×2) and dried over magnesium sulfate. Removal of solvent gave the dark red residue, which was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1/3) to afford 3.86 g (79%) of the title compound as a yellow solid.

Workup

  1. temperaturewas refluxed for 3 h
  2. concentrationthe mixture was concentrated
  3. customdried in vacuo
  4. dissolutionThe mixture was dissolved in ethyl acetate (300 ml)
  5. washwashed with water (100 ml) and saturated aqueous sodium bicarbonate (100 ml×2)
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of solvent
  8. customgave the dark red residue, which
  9. customwas chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1/3)

Sources & evidence

ORD record
ord-1a7709c33ba34c6d86aaaa5e3f9ac4e8
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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