Ethyl Acetoacetate → 1-Acetoacetyl-6-methyl-1,2,3,4-tetrahydroquinoline

HRID 436374Notes

Reaction equation

HRID 436374 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2.[C:12](OCC)(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15]>C1(C)C(C)=CC=CC=1.N1C=CC=CC=1>[C:12]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([CH3:1])=[CH:11][CH:10]=2)[CH2:5][CH2:6][CH2:7]1)(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15]

Participants

5

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 666786-Methyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 214544361-Acetoacetyl-6-methyl-1,2,3,4-tetrahydroquinolineYield 36.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 7237O-XyleneSolvent

Procedure

A solution of 6-methyl-1,2,3,4-tetrahydroquinoline (3.0 g) and ethyl acetoacetate (2.8 g) in xylene (7.0 ml) containing 2 drops of dry pyridine was refluxed for 12 hours. The solution was then allowed to cool to room temperature, washed in turn with 2N hydrochloric acid (2× 20 ml) and water (2 × 20 ml), dried over anhydrous magnesium sulphate and evaporated under reduced pressure at 100° to dryness, yielding 1-acetoacetyl-6-methyl-1,2,3,4-tetrahydroquinoline (1.7 g) as a crude solid, to be used directly in the next stage.

Workup

  1. temperaturewas refluxed for 12 hours
  2. washwashed in turn with 2N hydrochloric acid (2× 20 ml) and water (2 × 20 ml)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customevaporated under reduced pressure at 100° to dryness

Sources & evidence

ORD record
ord-8fd067d7f9cf4adc91d33fcaadf9eabf
Source dataset
uspto-grants-1977_02
Patent number
US04008325

Reaction notes

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