O-Xylene → HCID 19972556, compound

HRID 1382216Notes

Reaction equation

HRID 1382216 reaction equation
[CH3:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([C:13](Cl)=[O:14])[CH:7]=[CH:8][CH:9]=2)[O:4][C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(C)C(C)=CC=CC=1>C(Cl)(Cl)Cl.[Pd]>[CH3:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([CH:13]=[O:14])[CH:7]=[CH:8][CH:9]=2)[O:4][C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 7237O-XyleneHCID 13122092HCID 13122092, compound

Product 1

HCID 19972556HCID 19972556, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 59.74 g of 3-methyl-8-chlorocarbonylflavone (obtained from 3-methylflavon-8-carboxylic acid and thionyl chloride, white crystals, m.p. 156°-156.5° C.), 200 ml of xylene, 6 g of 5% palladium on barium sulfate and 0.4 ml of quinoline-S, maintained under stirring and under hydrogen flow, was heated for 6-7 hours at 85°-90° C. Upon completion of the reaction, the mixture was cooled, diluted with chloroform (20 ml), filtered, the solvent was evaporated under vacuum, and 260 ml of 20% sodium hydrogensulfite (W/V) and 600 ml of water were added to the residue. The mixture thus obtained was heated at reflux for 2 hours and then filtered while hot. The cooled filtrate was extracted several times with ethyl ether (4×200 ml), concentrated hydrogen chloride added and then heated to 95°-100° C. for 2 hours. After cooling, the solid thus formed was filtered and washed with water. The product (II) was obtained in a global yield equal to 78% of theoretical (41.46 g) and could be used as such in further syntheses. After recrystallization from methyl-tert-butyl-ether, it melted at 124°-126° C.

Workup

  1. temperaturemaintained
  2. temperaturewas heated for 6-7 hours at 85°-90° C
  3. customUpon completion of the reaction
  4. temperaturethe mixture was cooled
  5. filtrationfiltered
  6. customthe solvent was evaporated under vacuum, and 260 ml of 20% sodium hydrogensulfite (W/V) and 600 ml of water
  7. additionwere added to the residue
  8. customThe mixture thus obtained
  9. temperaturewas heated
  10. temperatureat reflux for 2 hours
  11. filtrationfiltered while hot
  12. extractionThe cooled filtrate was extracted several times with ethyl ether (4×200 ml), concentrated hydrogen chloride
  13. additionadded
  14. temperatureheated to 95°-100° C. for 2 hours
  15. temperatureAfter cooling
  16. customthe solid thus formed
  17. filtrationwas filtered
  18. washwashed with water

Sources & evidence

ORD record
ord-c165d9e7815d4e12b10db56990d6237d
Source dataset
uspto-grants-1989_02
Patent number
US04806534

Reaction notes

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