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

HRID 904309Notes

Reaction equation

HRID 904309 reaction equation
[C:1]1([C:7]2[C:8](=[O:19])[O:9][C:10]3[C:15]([C:16]=2[OH:17])=[CH:14][CH:13]=[CH:12][C:11]=3[OH:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27]Cl)[CH2:22][CH2:21]1>>[OH:18][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[O:9][C:8](=[O:19])[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[C:16]2[O:17][CH2:27][CH2:26][N:23]1[CH2:24][CH2:25][O:20][CH2:21][CH2:22]1

Participants

3

Reactant 2

HCID 767274-(2-Chloroethyl)morpholineHCID 547213333-Phenyl-4,8-dihydroxy-coumarin

Product 1

HCID 233340338-Hydroxy-4-(2'-morpholinoethoxy)-3-phenyl-coumarinYield 60.2%

Procedure

Prepared as described in Example 30 from 45.9 g. (0.18 mol) of 3-phenyl-4,8-dihydroxy-coumarin and 31.5 g. (0.21 mol) of 2-morpholino-1-chloroethane. After recrystallisation from ethane, 39.8 g. of a white substance are obtained; M.P. 190°-191° C. Yield 60.2% (theoretical yield 66 g.).

Workup

  1. customPrepared
  2. customAfter recrystallisation from ethane, 39.8 g
  3. customof a white substance are obtained

Sources & evidence

ORD record
ord-52b8dbae60f74fa48044aacda589d442
Source dataset
uspto-grants-1980_10
Patent number
US04230850

Reaction notes

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