Formaldehyde → Methyl 2-(quinolin-6-yl)acrylate

HRID 1512073Notes

Reaction equation

HRID 1512073 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C=O.[C:18]([O-])([O-])=O.[K+].[K+]>S([O-])(O)(=O)=O.C([N+](C)(C)C)CCCCCCCCCCCCCCC.C1(C)C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11](=[CH2:18])[C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 1514202Methyl 6-quinolineacetate

Product 1

HCID 67368576Methyl 2-(quinolin-6-yl)acrylateYield 86.3%

Reagents, catalysts & solvents 2

HCID 1097631-Hexadecanaminium, N,N,N-trimethyl-, sulfate (1:1)CatalystHCID 1140TolueneSolvent

Procedure

As shown in step ii of Scheme 1, methyl 2-(quinolin-6-yl)acetate (82 g, 407.5 mmol), paraformaldehyde (25.89 g, 862.1 mmol), K2CO3 (101.4 g, 733.5 mmol), and hexadecyl(trimethyl)ammonium hydrogen sulfate (15.55 g, 40.75 mmol) were taken up in toluene (1.6 liters) and refluxed for 2 hours until the starting material was completely consumed, as monitored by HPLC. The reaction mixture was cooled down using an ice-water bath and filtered through diatomaceous earth. The filtrate was washed with 1 liter of water and the organic layer dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure to afford methyl 2-(quinolin-6-yl)acrylate as a clear colorless oil (75.0 g). This material was used immediately without further purification in the next reaction.

Workup

  1. temperaturerefluxed for 2 hours until the starting material
  2. customwas completely consumed
  3. temperatureThe reaction mixture was cooled down
  4. filtrationfiltered through diatomaceous earth
  5. washThe filtrate was washed with 1 liter of water
  6. dry with materialthe organic layer dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-bb096a718bdb4f8d969d2c257c3b364d
Source dataset
uspto-grants-2012_07
Patent number
US08217056B2

Reaction notes

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