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

HRID 1607610Notes

Reaction equation

HRID 1607610 reaction equation
Cl[CH2:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=2)[NH:7][CH:6]=1)=[O:4].C(N)=[O:23].O>O1CCOCC1>[OH:23][CH2:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=2)[NH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 108919123-Chloroacetyl-5-(benzyloxy)indoleHCID 13001166Formamide--water (1/1)

Product 1

HCID 141683033-Hydroxyacetyl-5-(benzyloxy)indoleYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 19 in dioxane was added to formamide-water (10:1) and the mixture was stirred at 110° C. for 6.5 hrs., then was worked up as for 12 above. Purification by column chromatography gave 20 (55%) whose structure was established by spectral data. Calcd for C17H15NO3 : 281.1052 Found: 281.1052 (HREIMS).

Workup

  1. customPurification by column chromatography

Sources & evidence

ORD record
ord-321b918c849a4c6e8261e37ca3c00cd7
Source dataset
uspto-grants-1989_09
Patent number
US04866084

Reaction notes

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