Phosphorus oxychloride → HCID 12985698, compound

HRID 2119618Notes

Reaction equation

HRID 2119618 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:17])[C:13]=2[C:14](O)=O)[CH:5]=[CH:6][CH:7]=1.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:14]1[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[N:8]=[C:9]2[CH:10]=[N:11][N:12]([CH3:17])[C:13]=12.[Cl:20][C:14]1[C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=2[N:8]=[C:9]2[CH:10]=[N:11][N:12]([CH3:17])[C:13]=12

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12985697HCID 12985697, compound

Product 2

HCID 12985698HCID 12985698, compoundYield 40%HCID 12985699HCID 12985699, compoundYield 24%

Procedure

A mixture of 4-[(3-fluorophenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid (EXAMPLE 3, step 1, 470 mg, 2.00 mmol) in phosphorus oxychloride (10 ml) was refluxed for 3 h. After cooling to room temperature, the mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (100 ml), washed with water (30 ml) and saturated aqueous sodium bicarbonate (30 ml×2) and dried over magnesium sulfate. Removal of solvent gave a dark red residue, which was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:5) to afford 189 mg (40%) of the 9-chloro-6-fluoro-1-methyl-1H-pyrazolo[4,3-b]quinoline as a pale yellow solid and 111 mg (24%) of the 9-chloro-8-fluoro-1-methyl-1H-pyrazolo[4,3-b]quinoline as a yellow solid.

Workup

  1. temperaturewas refluxed for 3 h
  2. concentrationthe mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  4. washwashed with water (30 ml) and saturated aqueous sodium bicarbonate (30 ml×2)
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of solvent
  7. customgave a dark red residue, which
  8. customwas chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:5)

Sources & evidence

ORD record
ord-0c0f5f7242bb400995dec16d459aa712
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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