Vanillin → HCID 70491162, compound

HRID 464327Notes

Reaction equation

HRID 464327 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][C:19]([OH:20])=[C:16]([O:17][CH3:18])[CH:15]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>[Cl-].[Zn+2].[Cl-]>[C:23]([O:20][C:19]1[CH:21]=[CH:22][C:14](/[CH:13]=[C:6]2\[CH2:7][CH2:8][CH2:9][C:10]3[CH:11]=[C:2]([CH3:1])[CH:3]=[N:4][C:5]\2=3)=[CH:15][C:16]=1[O:17][CH3:18])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 1183VanillinHCID 7918Acetic AnhydrideHCID 1200283-Methyl-5,6,7,8-tetrahydroquinoline

Product 1

HCID 70491162HCID 70491162, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A mixture of 5,6,7,8-tetrahydro-3-methylquinoline (20 ml), vanillin (25 g), acetic anhydride (50 ml), and zinc chloride (1 g) was heated at reflux for 30 hours. The solvent was removed by evaporation and the residue was dissolved in ethyl acetate. This solution was shaken with 2N HCl and a crystalline solid was deposited. This was removed by filtration, washed with diethyl ether and propan-2-ol/diethyl ether. The product was then dried to give the title compound as the hydrochloride salt (34 g) m.p. 223°-5° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 hours
  3. customThe solvent was removed by evaporation
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. customThis was removed by filtration
  6. washwashed with diethyl ether and propan-2-ol/diethyl ether
  7. customThe product was then dried

Sources & evidence

ORD record
ord-ff3e1161d4a34c08815e6f49c2bd4273
Source dataset
uspto-grants-1985_10
Patent number
US04547510

Reaction notes

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