Benzoyl chloride → HCID 14032556, compound

HRID 1382572Notes

Reaction equation

HRID 1382572 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31]>CCOCC>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31].[C:18]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:10]=2)[C:6]([CH:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[N:7]1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 444972Fumaric AcidHCID 178480245HCID 178480245, compound

Product 1

HCID 14032556HCID 14032556, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of 3.1 g of 6-fluoro-3-(1-methyl-4-piperidinyl)-1H-indazole and 8 ml of benzoyl chloride was heated at 100° C. in a steam bath for 8 hrs. After cooling, ether was added and the solid was collected. The solid was treated with ammonium hydroxide solution to give an oil. The oil was dissolved in 300 ml of ether, stirred and 1.2 g of fumaric acid was added. After four hrs at ambient temperature, the fumarate salt was collected. Recrystallization from ethanol-ether yielded 3.0 g (50.9%) of product, mp 180°-182° C.

Workup

  1. temperatureAfter cooling
  2. customthe solid was collected
  3. additionThe solid was treated with ammonium hydroxide solution
  4. customto give an oil
  5. customthe fumarate salt was collected
  6. customRecrystallization from ethanol-ether

Sources & evidence

ORD record
ord-2727e706b4cb463ea9ca420e5649c6ee
Source dataset
uspto-grants-1989_02
Patent number
US04806649

Reaction notes

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