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

HRID 866657Notes

Reaction equation

HRID 866657 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 120 ml of dioxane and 11.2 ml of acetyl chloride cooled in an ice bath and then a mixture of 22 g of 5-chloro-1H-indole in 120 ml of dioxane was added thereto while keeping the temperature at 10° to 15° C. The mixture was then stirred for 7 hours at room temperature and protected from the light and the mixture was poured into 500 ml of water. The resulting mixture was stirred for 5 minutes and then another 500 ml of water were added thereto. The mixture was filtered and the product was empasted with 40 ml of acetonitrile and then was filtered. The product was rinsed with acetonitrile and once with ether to obtain 13.5 g of 1-acetyl-4-(5-chloro-[1H]-indol-3-yl)-1,4-dihydro-pyridine in the form of a pale yellow solid melting at 202° C.

Workup

  1. temperaturecooled in an ice bath
  2. additionwas added
  3. customat 10° to 15° C
  4. stirringThe resulting mixture was stirred for 5 minutes
  5. filtrationThe mixture was filtered
  6. filtrationwas filtered
  7. washThe product was rinsed with acetonitrile and once with ether

Sources & evidence

ORD record
ord-960f8811374d436c8a34e2cec1774efb
Source dataset
uspto-grants-1978_07
Patent number
US04100291

Reaction notes

Loading…