Benzoyl chloride, 3-nitro- → HCID 178519604, compound

HRID 485754Notes

Reaction equation

HRID 485754 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([OH:10])=[N:2]1.[N+:11]([C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17](Cl)=[O:18])([O-:13])=[O:12]>N1C=CC=CC=1>[N+:11]([C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([OH:10])=[N:2]1)=[O:18])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 81829Indazolinone

Product 1

HCID 178519604HCID 178519604, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
95 °C

Procedure

To 16.0 (0.118 mol) of 1H-indazol-3-ol dissolved in 120 ml of dry pyridine was added 21.8 g (0.118 mol) of m-nitrobenzoyl chloride. The heterogeneous yellow mixture was heated at 95° C. for 21/2 hrs. then let cool to room temperature and poured onto 1 liter of ice/H2O. The light yellow precipitate was collected, washed well with H2O and air-dried. Recrystallization from aqueous EtOH afforded 12.7 g (27.9%) of 1-(m-nitrobenzoyl)-1H-indazol-3-ol as a colorless solid, mp 232°-234° C.

Workup

  1. temperaturethen let cool to room temperature
  2. customThe light yellow precipitate was collected
  3. washwashed well with H2O
  4. customair-dried
  5. customRecrystallization from aqueous EtOH

Sources & evidence

ORD record
ord-4f50bcac5f2b4767b85e16cd0a171724
Source dataset
uspto-grants-1985_08
Patent number
US04537966

Reaction notes

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