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

HRID 904301Notes

Reaction equation

HRID 904301 reaction equation
[C:1]1([C:7]2[C:8](=[O:20])[O:9][C:10]3[C:15]([C:16]=2[OH:17])=[CH:14][CH:13]=[CH:12][C:11]=3[O:18][CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28]Cl)[CH2:23][CH2:22]1>>[CH3:19][O:18][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[O:9][C:8](=[O:20])[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[C:16]2[O:17][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 74%

Procedure

This compound is prepared according to the method of Example 8 from 45.6 g. (0.17 mol) of 3-phenyl-4-hydroxy-8-methoxy-coumarin and 30.5 g. (0.24 mol) of 2-morpholino-1-chlorethane. After recrystallisation from isopropanol, 48 g. are isolated; M.P. 90°-91° C. Yield 74% (theoretical yield 65.0 g.).

Workup

  1. customThis compound is prepared
  2. customAfter recrystallisation from isopropanol, 48 g
  3. customare isolated

Sources & evidence

ORD record
ord-60732d1f90384e999de23be4b8813069
Source dataset
uspto-grants-1980_10
Patent number
US04230850

Reaction notes

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