Benzaldehyde → HCID 53964573, compound

HRID 482888Notes

Reaction equation

HRID 482888 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:16])=[N:8][C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=2[CH:15]=1)=[O:5])[CH3:2].[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(OC(=O)C)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:16])=[N:8][C:9]2[C:10](=[CH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:11][CH2:12][CH2:13][C:14]=2[CH:15]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 13579990HCID 13579990, compound

Product 1

HCID 53964573HCID 53964573, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 5,6,7,8-tetrahydro-2-methyl-3-quinolinecarboxylic acid ethyl ester (4.4 g) and benzaldehyde (2.54 g) in acetic anhydride (13 ml) is heated at reflux temperature for 5 hours. The residue from evaporation is dissolved in aqueous tetrahydrofuran, diluted with water, and the precipitate is extracted into ethyl acetate. The extract is washed with 5 percent sodium bicarbonate solution, dried and evaporated. The residue deposited pure 5,6,7,8-tetrahydro-2-methyl-8-(phenylmethylene)-3-quinolinecarboxylic acid ethyl ester (3.0 g, m.p. 125° C.-126° C.) from ethanol solution.

Workup

  1. temperatureat reflux temperature for 5 hours
  2. customThe residue from evaporation
  3. dissolutionis dissolved in aqueous tetrahydrofuran
  4. additiondiluted with water
  5. extractionthe precipitate is extracted into ethyl acetate
  6. washThe extract is washed with 5 percent sodium bicarbonate solution
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-9a1f708f767b4a9ea85ec5fb8dbd61b3
Source dataset
uspto-grants-1986_03
Patent number
US04576949

Reaction notes

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