Water → 1-[4-(5-Chloro-1H-indol-3-yl)pyridin-1(4H)-yl]ethan-1-one

HRID 2049022Notes

Reaction equation

HRID 2049022 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:7](Cl)(=[O:9])[CH3:8].[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[CH:15]2.O>O1CCOCC1>[C:7]([N:1]1[CH:6]=[CH:5][CH:4]([C:15]2[C:14]3[C:18](=[CH:19][CH:20]=[C:12]([Cl:11])[CH:13]=3)[NH:17][CH:16]=2)[CH:3]=[CH:2]1)(=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 1049PyridineHCID 6367Acetyl chlorideHCID 871105-Chloroindole

Product 1

HCID 128313731-[4-(5-Chloro-1H-indol-3-yl)pyridin-1(4H)-yl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

27 ml of redistilled pyridine were added at an interior temperature of 8° to 15° C. to a mixture of 11.2 ml of acetyl chloride and 120 ml of dioxane cooled in an ice bath and a mixture of 22 g of 5-chloro-1H-indole in 120 ml of dioxane was added to the resulting suspension at 10° to 15° C. The mixture was stirred in the dark at room temperature for 7 hours and the suspension was poured into 500 ml of water. The mixture was stirred for 5 minutes and another 500 ml of water were added. The mixture was filtered and the recovered solid was empasted with 40 ml of acetonitrile, was filtered, rinsed with acetonitrile and once with ether to obtain 13.5 g of 3-(1-acetyl-1,4-dihydro-4-pyridyl)-5-chloro-1H-indole in the form of a pale yellow solid melting at 202° C.

Workup

  1. temperaturecooled in an ice bath
  2. additionwas added to the resulting suspension at 10° to 15° C
  3. stirringThe mixture was stirred for 5 minutes
  4. filtrationThe mixture was filtered
  5. filtrationwas filtered
  6. washrinsed with acetonitrile and once with ether

Sources & evidence

ORD record
ord-105c737060f84a39bcb5f35ec17ac5ee
Source dataset
uspto-grants-1980_04
Patent number
US04196209

Reaction notes

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