Ethyl 2-methylacetoacetate → HCID 178442067, compound

HRID 1831722Notes

Reaction equation

HRID 1831722 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. customAfter the solvent was evaporated
  3. temperaturethe resultant intermediate was refluxed in diphenyl ether for 30 minutes
  4. temperatureto cool
  5. customto produce
  6. customprecipitates
  7. filtrationwhich were collected by filtration under reduced pressure

Sources & evidence

ORD record
ord-199f30a3bc36415c83271102c246859a
Source dataset
uspto-grants-2006_06
Patent number
US07067668B2

Reaction notes

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