4-Hydroxybenzaldehyde → HCID 54101020, compound

HRID 482887Notes

Reaction equation

HRID 482887 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].[OH:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:16])=[N:8][C:9]2[C:10](=[CH:22][C:21]3[CH:24]=[CH:25][C:18]([O:17][C:26](=[O:28])[CH3:27])=[CH:19][CH:20]=3)[CH2:11][CH2:12][CH2:13][C:14]=2[CH:15]=1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 7918Acetic AnhydrideHCID 13579990HCID 13579990, compound

Product 1

HCID 54101020HCID 54101020, compound

Procedure

A solution of 5,6,7,8-tetrahydro-2-methyl-3-quinolinecarboxylic acid ethyl ester (2.19 g) and 4-hydroxybenzaldehyde (1.32 g, 11 mmol) in acetic anhydride (6.5 ml) is heated at reflux temperature for 18 hours. The solution is evaporated, the residue dissolved in tetrahydrofuran and crude 8-[[4-(acetyloxy)phenyl)methylene]-5,6,7,8-tetrahydro-2-methyl-3-quinolinecarboxylic acid ethyl ester is precipitated with water to yield 3.4 g. Purification on silica gel (250 g) with 9:1 Skelly B:ethyl acetate gives pure 8-[[4-(acetyloxy)phenyl)-methylene]-5,6,7,8-tetrahydro-2-methyl-3-quinolinecarboxylic acid ethyl ester (2.76 g), m.p. 112° C., after ethanol crystallization.

Workup

  1. temperatureat reflux temperature for 18 hours
  2. customThe solution is evaporated
  3. dissolutionthe residue dissolved in tetrahydrofuran
  4. customcrude 8-[[4-(acetyloxy)phenyl)methylene]-5,6,7,8-tetrahydro-2-methyl-3-quinolinecarboxylic acid ethyl ester is precipitated with water
  5. customto yield 3.4 g
  6. customPurification on silica gel (250 g) with 9:1 Skelly B

Sources & evidence

ORD record
ord-25203c70e36f4b52bb76e7fe3277e277
Source dataset
uspto-grants-1986_03
Patent number
US04576949

Reaction notes

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