2-Methoxybenzaldehyde → HCID 70491447, compound

HRID 464329Notes

Reaction equation

HRID 464329 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]([O:19][CH3:20])=[CH:15][CH:16]=[CH:17][CH:18]=1>C(OC(=O)C)(=O)C>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][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

Participants

4

Reactant 2

HCID 86582-MethoxybenzaldehydeHCID 1200283-Methyl-5,6,7,8-tetrahydroquinoline

Product 1

HCID 70491447HCID 70491447, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

5,6,7,8-Tetrahydro-3-methylquinoline (6.6 g) was added to o-anisaldehyde (8.16 g) in acetic anhydride (10 ml) and was heated to reflux for 14 hours after which the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (50 ml) and was added to 2N HCl (150 ml), the aqueous layer was basified (Na2CO3) and extracted with ethyl acetate (4×100 ml) dried (MgSO4) and evaporated under reduced pressure. The residue was washed with several aliquots of hot hexane and was then dissolved in a small volume of boiling propan-2-ol and etherial hydrogen chloride was added in excess. On cooling a precipitate formed and was removed by filtration, washed with ether and dried under vacuum to give the title compound as the hydrochloride salt (2.6 g) m.p. 221°-222.5° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 14 hours after which the solvent
  3. customwas removed under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  5. additionwas added to 2N HCl (150 ml)
  6. extractionextracted with ethyl acetate (4×100 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure
  9. washThe residue was washed with several aliquots of hot hexane
  10. dissolutionwas then dissolved in a small volume of boiling propan-2-ol and etherial hydrogen chloride
  11. additionwas added in excess
  12. temperatureOn cooling a precipitate
  13. customformed
  14. customwas removed by filtration
  15. washwashed with ether
  16. customdried under vacuum

Sources & evidence

ORD record
ord-2431f941a04141c0b4fbca348731a5f0
Source dataset
uspto-grants-1985_10
Patent number
US04547510

Reaction notes

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