Furfural → HCID 54232925, compound

HRID 482892Notes

Reaction equation

HRID 482892 reaction equation
[CH3:1][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH:20]=O.[C:22]([O-])(=O)[CH3:23].[Na+]>C(OC(=O)C)(=O)C>[CH2:22]([O:13][C:12]([C:11]1[C:2]([CH3:1])=[N:3][C:4]2[C:5](=[CH:20][C:16]3[O:15][CH:19]=[CH:18][CH:17]=3)[CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=1)=[O:14])[CH3:23]

Participants

5

Reactant 3

HCID 7362FurfuralHCID 517045Sodium AcetateHCID 13579997HCID 13579997, compound

Product 1

HCID 54232925HCID 54232925, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 5,6,7,8-tetrahydro-2-methyl-3-quinolinecarboxylic acid (2.19 g) in acetic anhydride (10 ml) is treated with 2-furaldehyde (1.0 ml) and sodium acetate (0.82 g). The solution is treated at reflux temperature for 24 hours. The residue from the solvent evaporation is dissolved in ethyl acetate, washed with brine solution, dried and evaporated to a semi-crystalline residue (30 g). Filtration through silica gel (150 g) with 9:1 Skelly B:ethyl acetate gives 8-(2-furanylmethylene)-5,6,7,8-tetrahydro-2-methyl-3-quinolinecarboxylic acid ethyl ester (1.40 g), m.p. 119° C.-120° C. after hexane crystallization.

Workup

  1. additionThe solution is treated
  2. temperatureat reflux temperature for 24 hours
  3. customThe residue from the solvent evaporation
  4. dissolutionis dissolved in ethyl acetate
  5. washwashed with brine solution
  6. customdried
  7. customevaporated to a semi-crystalline residue (30 g)
  8. filtrationFiltration through silica gel (150 g) with 9:1 Skelly B

Sources & evidence

ORD record
ord-2f27f16b93f64beeb7b56a82adc7a75a
Source dataset
uspto-grants-1986_03
Patent number
US04576949

Reaction notes

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