o-Vanillin → HCID 136387267, compound

HRID 464330Notes

Reaction equation

HRID 464330 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.O=[CH:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:17]([O:18][CH3:19])[C:15]=1[OH:16]>[Cl-].[Cl-].[Zn+2].C(OC(=O)C)(=O)C>[OH:16][C:15]1[C:17]([O:18][CH3:19])=[CH:20][CH:21]=[CH:22][C:14]=1/[CH:13]=[C:6]1\[CH2:7][CH2:8][CH2:9][C:10]2[CH:11]=[C:2]([CH3:1])[CH:3]=[N:4][C:5]\1=2

Participants

5

Reactant 2

HCID 8991o-VanillinHCID 1200283-Methyl-5,6,7,8-tetrahydroquinoline

Product 1

HCID 136387267HCID 136387267, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

5,6,7,8-Tetrahydro-3-methylquinoline (20 ml), o-vanillin (25 g), acetic anhydride (50 ml), and ZnCl2 (1 g) were heated at reflux for 17 hours. The solvent was removed by evaporation and the residue was dissolved in ethyl acetate (100 ml) and acidified with 2N HCl solution. The solid obtained was removed by filtration and the aqueous layer was basified with Na2CO3 and shaken with diethyl ether. A solid was obtained in the ether layer which was removed by filtration. The combined solids were dissolved in 1N sodium hydroxide and the solution was extracted with ethyl acetate. The extracts were dried over MgSO4 and the solvent was removed by evaporation. The crystals obtained were washed with hexane and dried to give the title compound (6 g) m.p. 149°-153° C.

Workup

  1. temperatureat reflux for 17 hours
  2. customThe solvent was removed by evaporation
  3. dissolutionthe residue was dissolved in ethyl acetate (100 ml)
  4. customThe solid obtained
  5. customwas removed by filtration
  6. customA solid was obtained in the ether layer which
  7. customwas removed by filtration
  8. dissolutionThe combined solids were dissolved in 1N sodium hydroxide
  9. extractionthe solution was extracted with ethyl acetate
  10. dry with materialThe extracts were dried over MgSO4
  11. customthe solvent was removed by evaporation
  12. customThe crystals obtained
  13. washwere washed with hexane
  14. customdried

Sources & evidence

ORD record
ord-7d6be5ab8e4a4677a1b1120eb0be09be
Source dataset
uspto-grants-1985_10
Patent number
US04547510

Reaction notes

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