2-Thiophenecarboxaldehyde → HCID 54408924, compound

HRID 482893Notes

Reaction equation

HRID 482893 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].C([O-])(=O)C.[Na+].[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH:27]=O>C(OC(=O)C)(=O)C.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:16])=[N:8][C:9]2[C:10](=[CH:27][C:23]3[S:22][CH:26]=[CH:25][CH:24]=3)[CH2:11][CH2:12][CH2:13][C:14]=2[CH:15]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 73642-ThiophenecarboxaldehydeHCID 517045Sodium AcetateHCID 13579990HCID 13579990, compound

Product 1

HCID 54408924HCID 54408924, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 5,6,7,8-tetrahydro-2-methyl-3-quinolinecarboxylic acid ethyl ester as prepared in Preparation I (3.66 g) in acetic anhydride (10 ml) is treated with sodium acetate (1.37 g) and 2-thiophenecarboxaldehyde (2.24 g). The solution is heated at reflux temperature for 56 hours. The cooled mixture is diluted with toluene, filtered and the filtrate evaporated to a solid residue. The residue is triturated with hexane and filtered to yield a residue of 5,6,7,8-tetrahydro-2-methyl-8-(2-thienylmethylene)-3-quinoline carboxylic acid ethyl ester (1.91 g) m.p. 117° C.-118° C. The filtrate residue is purified on silica gel (70 g) with 9:1 Skelly B:ethyl acetate as eluent. Fractions 7-13, 20 ml each, provide additional 5,6,7,8-tetrahydro-2-methyl-8-(2-thienylmethylene)-3-quinoline carboxylic acid ethyl ester (0.73 g). An analytical sample, m.p. 117° C.-118° C. is obtained by hexane recrystallization.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux temperature for 56 hours
  3. filtrationfiltered
  4. customthe filtrate evaporated to a solid residue
  5. customThe residue is triturated with hexane
  6. filtrationfiltered

Sources & evidence

ORD record
ord-2ae796e24e5c492fafa34f82123504e7
Source dataset
uspto-grants-1986_03
Patent number
US04576949

Reaction notes

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