Chloroacetyl chloride → 3-Chloroacetyl-6-(benzyloxy)indole

HRID 1607607Notes

Reaction equation

HRID 1607607 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18][CH2:19][C:20](Cl)=[O:21].C(OCC)C.O>O1CCOCC1.N1C=CC=CC=1>[Cl:18][CH2:19][C:20]([C:13]1[C:12]2[C: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][CH:11]=2)[NH:15][CH:14]=1)=[O:21]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 2608046-(benzyloxy)-1H-indoleHCID 21584184Diethylether water

Product 1

HCID 109026373-Chloroacetyl-6-(benzyloxy)indoleYield 47%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent2×

Procedure

6-(Benzyloxy)indole dissolved in a mixture of dioxane and pyridine was stirred at 60 C. under nitrogen while chloroacetyl chloride in dioxane was added dropwise during 1 hr. The reaction mixture was then stirred for another 0.5 hr. and poured into diethyl ether-water. The precipitate was collected by filtration and washed thoroughly with cold diethyl ether to yield 47% of 11 as an orange solid.

Workup

  1. stirringThe reaction mixture was then stirred for another 0.5 hr
  2. filtrationThe precipitate was collected by filtration
  3. washwashed thoroughly with cold diethyl ether

Sources & evidence

ORD record
ord-94aa245d38e149fb953fc07f3d16d9e3
Source dataset
uspto-grants-1989_09
Patent number
US04866084

Reaction notes

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