Thionyl Chloride → 4-(6-fluoro-3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoyl chloride

HRID 1817057Notes

Reaction equation

HRID 1817057 reaction equation
[F:1][C:2]1[C:11]2[N:10]=[N:9][C:8]3[C:12](=[O:24])[N:13]([C:15]4[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=4)[NH:14][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:27])=O>>[F:1][C:2]1[C:11]2[N:10]=[N:9][C:8]3[C:12](=[O:24])[N:13]([C:15]4[CH:23]=[CH:22][C:18]([C:19]([Cl:27])=[O:20])=[CH:17][CH:16]=4)[NH:14][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 589748824-(6-fluoro-3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoic acid

Product 1

HCID 589748584-(6-fluoro-3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoyl chloride

Conditions

Temperature
70 °C

Procedure

Crude 4-(6-fluoro-3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)-benzoic acid (1.45 g) from the previous stage was dissolved in thionyl chloride (50 ml). The mixture was heated to 70° C. for 2-3 h until no further gas evolution was observed. The mixture was cooled to room temperature and excess thionyl chloride was removed under vacuum. The residues were azeotroped with toluene (2×20 ml) to give a solid. The solid was collected by filtration, washed with toluene and dried under vacuum. The product was isolated as a yellow powder (670 mg, 1.95 mmol). LCMS: m/z [M+H]+ 339 (methyl ester resulting from sample make-up in methanol).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customexcess thionyl chloride was removed under vacuum
  3. customThe residues were azeotroped with toluene (2×20 ml)
  4. customto give a solid
  5. filtrationThe solid was collected by filtration
  6. washwashed with toluene
  7. customdried under vacuum

Sources & evidence

ORD record
ord-dd03dde8f5b54cfba70c68885066bba6
Source dataset
uspto-grants-2009_10
Patent number
US07598247B2

Reaction notes

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