Hydrochloric Acid → HCID 20452422, compound

HRID 1462952Notes

Reaction equation

HRID 1462952 reaction equation
[CH3:1][N:2]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[OH:20])=O)=[CH:6][CH:5]=1)[CH3:3].Cl.Cl.CN(C1C=CC(C2CC(=O)C3C(=CC=CC=3)O2)=CC=1)C>O.[Zn]>[CH3:1][N:2]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:11][CH2:12][C:14]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[O:20]2)=[CH:6][CH:5]=1)[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 978474-(N,N-dimethylamino)-2'-hydroxychalconeHCID 70503585HCID 70503585, compound

Product 1

HCID 20452422HCID 20452422, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

4-(N,N-dimethylamino)-2'-hydroxychalcone (6.6 g.) was boiled under reflux with 2-N hydrochloric acid (100 ml.) for 3 hrs. The resulting solution of 4'-(N,N-dimethylamino) flavanone hydrochloride was added to a suspension of amalgamated zinc (from zinc powder (40 g.) and mercuric chloride (0.8 g.)) in water 30 ml. and the mixture stirred at 45° C. for 45 min. The residual zinc was separated by decantation from the aqueous liquor, stirred with acetic acid (150 ml.) and filtered. The zinc was further washed with acetic acid and the combined washing and filtrate were diluted with water and extracted with toluene. The extract was washed with water, dried over magnesium sulphate, filtered and evaporated. The residue was chromatographed on neutral alumina and the first fraction evaporated to give crystalline 4'-(N,N-dimethylamino) flavan which was recrystallised from methanol, and then 60°-80° C. petroleum ether, 0.7 g., m.p. 77°-78° C.

Workup

  1. customThe residual zinc was separated by decantation from the aqueous liquor
  2. stirringstirred with acetic acid (150 ml.)
  3. filtrationfiltered
  4. washThe zinc was further washed with acetic acid
  5. washthe combined washing
  6. additionfiltrate were diluted with water
  7. extractionextracted with toluene
  8. washThe extract was washed with water
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was chromatographed on neutral alumina
  13. customthe first fraction evaporated

Sources & evidence

ORD record
ord-f23353365dd647b7a8d37e57bdca320c
Source dataset
uspto-grants-1984_07
Patent number
US04461907

Reaction notes

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