Pyridine → 3-Chloroacetyl-5-(benzyloxy)indole

HRID 1607609Notes

Reaction equation

HRID 1607609 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[Cl:24][CH2:25][C:26](Cl)=[O:27].C(OCC)C.O>O1CCOCC1>[Cl:24][CH2:25][C:26]([C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:10]=2)[NH:14][CH:13]=1)=[O:27]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 146245-BenzyloxyindoleHCID 21584184Diethylether water

Product 1

HCID 108919123-Chloroacetyl-5-(benzyloxy)indole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

5-(Benzyloxy)indole in dioxane containing pyridine was stirred for 1 hr. at 65° C. under nitrogen while chloroacetyl chloride in dioxane was added dropwise. The reaction mixture was stirred for another 1 hr., then poured into diethyl ether-water. The precipitate was collected by filtration and washed thoroughly with cold Et2O to yield 19, an orange solid.

Workup

  1. stirringThe reaction mixture was stirred for another 1 hr
  2. filtrationThe precipitate was collected by filtration
  3. washwashed thoroughly with cold Et2O

Sources & evidence

ORD record
ord-80b58256898549e4b404b9fe585b36dc
Source dataset
uspto-grants-1989_09
Patent number
US04866084

Reaction notes

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