Benzoyl chloride → HCID 14032596, compound

HRID 867737Notes

Reaction equation

HRID 867737 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=3)[NH:10][N:9]=2)[CH2:4][CH2:3]1.[C:20]([Cl:28])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCOCC>[ClH:28].[C:20]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[C:8]([CH:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[N:9]1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 178480242HCID 178480242, compound

Product 1

HCID 14032596HCID 14032596, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(1-methyl-4-piperidinyl)-5-nitro-1H-indazole (4.0 g, 0.015 mol) of Example 105 and benzoyl chloride (12 ml) was heated at 100° C. (steam bath) for 4 hours. After cooling to ambient temperature, ether was added, the mixture stirred for 1 hour and then 4.9 g of a solid was collected. The solid was recrystallized twice from DMF and once from methanol to yield 2.3 g (38%) of 1-benzoyl-3-(1-methyl-4-piperidinyl)-5-nitro-1H-indazole hydrochloride, mp 297°-299° C.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. custom4.9 g of a solid was collected
  3. customThe solid was recrystallized twice from DMF and once from methanol

Sources & evidence

ORD record
ord-52d4334954904a55b44a06805a375b9f
Source dataset
uspto-grants-1988_10
Patent number
US04775761

Reaction notes

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