4-(2-Chloroethyl)morpholine → 8-Methoxy-4-(2'-morpholinoethoxy)-3-phenyl-coumarin

HRID 904308Notes

Reaction equation

HRID 904308 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[O:11][C:10](=[O:13])[C:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[C:8]2[OH:20].[O:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28]Cl)[CH2:23][CH2:22]1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[O:11][C:10](=[O:13])[C:9]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[C:8]2[O:20][CH2:28][CH2:27][N:24]1[CH2:25][CH2:26][O:21][CH2:22][CH2:23]1

Participants

3

Reactant 2

HCID 767274-(2-Chloroethyl)morpholineHCID 547213328-Methoxy-4-hydroxy-3-phenylcoumarin

Product 1

HCID 233340708-Methoxy-4-(2'-morpholinoethoxy)-3-phenyl-coumarinYield 76%

Procedure

As in Example 8, 45.6 g. (0.17 mol) of 8-methoxy-4-hydroxy-3-phenyl-coumarin are treated with 30.5 g. (0.20 mol) of 2-morpholino-1-chlorethane. After evaporation of the chloroform and recrystallisation from isopropanol, 48 g. of a beige-coloured solid are obtained. M.P. 90°-91° C.; yield 76% (theoretical yield 63 g.).

Workup

  1. customAfter evaporation of the chloroform and recrystallisation from isopropanol, 48 g
  2. customof a beige-coloured solid are obtained

Sources & evidence

ORD record
ord-38183cca69984b55a5fd6844e6e176e0
Source dataset
uspto-grants-1980_10
Patent number
US04230850

Reaction notes

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