3,4-Dihydroxybenzaldehyde → HCID 70491734, compound

HRID 464324Notes

Reaction equation

HRID 464324 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.[OH:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[OH:21])[CH:16]=O>[Cl-].[Cl-].[Zn+2].C(OC(=O)C)(=O)C>[C:13]([O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][C:20](=[O:21])[CH3:19])/[CH:16]=[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:12])[CH3:14]

Participants

5

Reactant 2

HCID 87683,4-DihydroxybenzaldehydeHCID 1200283-Methyl-5,6,7,8-tetrahydroquinoline

Product 1

HCID 70491734HCID 70491734, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 7918Acetic AnhydrideSolvent2×

Procedure

A mixture of 5,6,7,8-tetrahydro-3-methylquinoline (20 ml), 3,4-dihydroxybenzaldehyde (20 g) and acetic anhydride (50 ml) was heated at 100° for 48 hours. Further acetic anhydride (50 ml) and ZnCl2 (1 g) were added and the mixture was heated at reflux for 16 hours. The solvent was removed by evaporation, the residue was neutralised (Na2CO3) in the presence of ethyl acetate and extracted with ethyl acetate. The ethyl acetate solution was extracted with 2N HCl and this extract was washed with ethyl acetate, basified (Na2CO3) and extracted with Et2O. The ether solution was dried (MgSO4) and evaporated and the residue triturated with hexane and recrystallised from di-isopropyl ether to give the title compound (22 g) m.p. 100°-1° 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. extractionextracted with ethyl acetate
  6. extractionThe ethyl acetate solution was extracted with 2N HCl
  7. washthis extract was washed with ethyl acetate
  8. extractionextracted with Et2O
  9. dry with materialThe ether solution was dried (MgSO4)
  10. customevaporated
  11. customthe residue triturated with hexane
  12. customrecrystallised from di-isopropyl ether

Sources & evidence

ORD record
ord-0c0db39a4df9404a9b0d3abf03bfbc82
Source dataset
uspto-grants-1985_10
Patent number
US04547510

Reaction notes

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