Ethyl 2-methylacetoacetate → HCID 178442067, compound

HRID 1840237Notes

Reaction equation

HRID 1840237 reaction equation
[CH2:1]([C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:13][CH:14]([C:20]([CH3:22])=O)[C:15](OCC)=[O:16]>C1C=CC=CC=1>[OH:16][C:15]1[C:8]2[C:9](=[CH:11][CH:12]=[C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH:7]=2)[N:10]=[C:20]([CH3:22])[C:14]=1[CH3:13]

Participants

4

Reactant 2

HCID 701Ethyl 2-methylacetoacetateHCID 931624-Pentylaniline

Product 1

HCID 178442067HCID 178442067, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1.63 Grams of 4-n-pentylaniline and 1.44 g of ethyl 2-methylacetoacetate were refluxed in benzene in the presence of a Lewis acid catalyst for 3 hours. The reaction mixture was washed with a saturated sodium hydrogencarbonate solution and a saturated brine and dried over anhydrous sodium sulfate. After the solvent was evaporated, the resultant intermediate was refluxed in diphenyl ether for 30 minutes and allowed to cool to produce precipitates, which were collected by filtration under reduced pressure to obtain 1.01 g of 4-hydroxy-2,3-dimethyl-6-n-pentyl-quinoline (yield 42%). Its NMR spectral data are shown in the following Table 2.

Workup

  1. washThe reaction mixture was washed with a saturated sodium hydrogencarbonate solution
  2. dry with materiala saturated brine and dried over anhydrous sodium sulfate
  3. customAfter the solvent was evaporated
  4. temperaturethe resultant intermediate was refluxed in diphenyl ether for 30 minutes
  5. temperatureto cool
  6. customto produce
  7. customprecipitates
  8. filtrationwhich were collected by filtration under reduced pressure

Sources & evidence

ORD record
ord-02ee5093fef0477cbc204598124b8ca8
Source dataset
uspto-grants-2004_01
Patent number
US06680282B2

Reaction notes

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