Acetic Acid → HCID 19835337, compound

HRID 478085Notes

Reaction equation

HRID 478085 reaction equation
C([N:8]([CH2:19][CH:20]([OH:40])[CH2:21][O:22][C:23]1[CH:32]=[C:31]2[C:26]([C:27](=[O:39])[CH:28]=[C:29]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[O:30]2)=[CH:25][CH:24]=1)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=1)C1C=CC=CC=1.C1CCCCC=1.C(O)(=O)C>O.[Pd]>[CH2:12]([CH2:11][CH2:10][CH2:9][NH:8][CH2:19][CH:20]([OH:40])[CH2:21][O:22][C:23]1[CH:32]=[C:31]2[C:26]([C:27](=[O:39])[CH:28]=[C:29]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[O:30]2)=[CH:25][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8079CyclohexeneHCID 198353387-[3-[N-benzyl,N-(3-nicotinylpropyl)amino]-2-hydroxypropoxy]flavone

Product 1

HCID 19835337HCID 19835337, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A suspension of 7-[3-[N-benzyl,N-(3-nicotinylpropyl)amino]-2-hydroxypropoxy]flavone (4.50 g, 8.64 mmol), Example 17b, palladium black (0.1 g), cyclohexene (30 ml), and acetic acid (30 ml) was refluxed for 6 hours. The solvent was evaporated to give a residue which was dissolved in water and washed with chloroform (twice) to remove impurities. The aqueous solution was basified with 2.5N NaOH and then extracted with methylene chloride several times. The extracts were washed with water, dried (MgSO4), and evaporated to afford a yellow solid of 2.9 g. Recrystallization from isopropyl alcohol gave light yellow crystals (2.0 g; 54% yield), mp 116°-119° C.

Workup

  1. temperaturewas refluxed for 6 hours
  2. customThe solvent was evaporated
  3. customto give a residue which
  4. washwashed with chloroform (twice)
  5. customto remove impurities
  6. extractionextracted with methylene chloride several times
  7. washThe extracts were washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto afford a yellow solid of 2.9 g
  11. customRecrystallization from isopropyl alcohol
  12. customgave light yellow crystals (2.0 g; 54% yield), mp 116°-119° C.

Sources & evidence

ORD record
ord-dcb435a1401249cc8b34b3d0d5a58566
Source dataset
uspto-grants-1989_12
Patent number
US04889941

Reaction notes

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