Salicylaldehyde → HCID 70490860, compound

HRID 464326Notes

Reaction equation

HRID 464326 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.[CH:12](=O)[C:13]1[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[OH:15].[C:21](OC(=O)C)(=[O:23])[CH3:22]>[Cl-].[Cl-].[Zn+2]>[C:21]([O:15][C:14]1[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=1/[CH:12]=[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)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 7918Acetic Anhydride2×HCID 1200283-Methyl-5,6,7,8-tetrahydroquinoline

Product 1

HCID 70490860HCID 70490860, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A mixture of 5,6,7,8-tetrahydro-3-methylquinoline (20 ml), salicylaldehyde (20 ml) and acetic anhydride (40 ml) was heated at 100° for 48 hours. Further acetic anhydride (50 ml) and ZnCl2 (1 g) was added and the mixture was heated at reflux for 16 hours. The solvent was removed by evaporation and the residue was dissolved in ethyl acetate, neutralised with Na2CO3 solution and extracted with ethyl acetate. The extracts were extracted with 2N HCl and the extract washed with ethyl acetate basified (Na2CO3) and extracted with diethyl ether. The solution was dried (MgSO4) and evaporated to give an oil which was triturated with n-hexane and recrystallised from n-hexane to give the title compound (12 g) m.p. 85°-7° C.

Workup

  1. temperaturewas heated at 100° for 48 hours
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 16 hours
  4. customThe solvent was removed by evaporation
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. extractionextracted with ethyl acetate
  7. extractionThe extracts were extracted with 2N HCl
  8. washthe extract washed with ethyl acetate
  9. extractionextracted with diethyl ether
  10. dry with materialThe solution was dried (MgSO4)
  11. customevaporated
  12. customto give an oil which
  13. customwas triturated with n-hexane
  14. customrecrystallised from n-hexane

Sources & evidence

ORD record
ord-a5a0304987ed456c82924f297c6aeef7
Source dataset
uspto-grants-1985_10
Patent number
US04547510

Reaction notes

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