N,N-Diethylaniline → HCID 13298918, compound

HRID 359498Notes

Reaction equation

HRID 359498 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12]CC=C)[O:8][C:7](=[O:16])[CH:6]=[CH:5]2.CCN([C:22]1[CH:23]=CC=C[CH:27]=1)CC>CCCCCC>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH2:23][CH:22]=[CH2:27])[C:11]=1[OH:12])[O:8][C:7](=[O:16])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 7061N,N-DiethylanilineHCID 13298915HCID 13298915, compound

Product 1

HCID 13298918HCID 13298918, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of 6-methyl-7-hydroxycoumarin (IV) (11.4 g) in diethylaniline (80 ml) was refluxed for 2 h. After cooling the solution was diluted with n-hexane (500 ml) yielding a precipitate, which was collected by filtration, washed several times with n-hexane and crystallized from EtOAc, yielding 6-methyl-7-hydroxy-8-allylcoumarin (VII) (6.3 g; m.p. 161°-2° C.). ##STR13##

Workup

  1. temperatureAfter cooling the solution
  2. customyielding a precipitate, which
  3. filtrationwas collected by filtration
  4. washwashed several times with n-hexane
  5. customcrystallized from EtOAc

Sources & evidence

ORD record
ord-4cac852744dd4a519f4bc27ce8199bf5
Source dataset
uspto-grants-1991_03
Patent number
US05001147

Reaction notes

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