Acetic Anhydride → HCID 70492022, compound

HRID 464331Notes

Reaction equation

HRID 464331 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.[C:12]([O:15][C:16](=[O:18])[CH3:17])(=O)[CH3:13]>[Cl-].[Cl-].[Zn+2]>[C:16]([O:15][C:12]1[CH:1]=[C:2]([CH:11]=[CH:10][CH:13]=1)/[CH:3]=[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:18])[CH3:17]

Participants

4

Reactant 2

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

Product 1

HCID 70492022HCID 70492022, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A mixture of 5,6,7,8-tetrahydro-3-methylquinoline (20 ml), m-hydroxybenzaldehyde (20 g), acetic anhydride (50 ml) and ZnCl2 (1 g) was heated at reflux for 31/2 hours. The solvent was removed by evaporation and the residue dissolved in ethyl acetate (300 ml). The solution was extracted with 2N HCl, and the acidic phase was washed once with ethyl acetate. It was then basified (Na2CO3) and the product extracted into a mixture of diethyl ether and ethyl acetate. The solvent was removed by evaporation and the residue crystallised from di-isopropyl ether, washed twice with hexane and then dried to give the title compound as the hemihydrate (7.4 g). m.p. 66°-8° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 31/2 hours
  3. customThe solvent was removed by evaporation
  4. dissolutionthe residue dissolved in ethyl acetate (300 ml)
  5. extractionThe solution was extracted with 2N HCl
  6. washthe acidic phase was washed once with ethyl acetate
  7. extractionthe product extracted into a mixture of diethyl ether and ethyl acetate
  8. customThe solvent was removed by evaporation
  9. customthe residue crystallised from di-isopropyl ether
  10. washwashed twice with hexane
  11. customdried

Sources & evidence

ORD record
ord-d40fb39d0aaf434cabf136b86d792358
Source dataset
uspto-grants-1985_10
Patent number
US04547510

Reaction notes

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