Methyl 2-pyridylacetate → 3-Ethylindolizine-1-carboxylic acid

HRID 1638974Notes

Reaction equation

HRID 1638974 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10]C)=[O:9].Br[CH:13]([CH2:16][CH3:17])[CH:14]=O>C1(C)C(C)=CC=CC=1>[CH2:16]([C:13]1[N:1]2[C:2]([CH:3]=[CH:4][CH:5]=[CH:6]2)=[C:7]([C:8]([OH:10])=[O:9])[CH:14]=1)[CH3:17]

Participants

4

Reactant 2

HCID 74264Methyl 2-pyridylacetateHCID 126178112-Bromobutanal

Product 1

HCID 147882723-Ethylindolizine-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of methyl 2-pyridylacetate (6 ml) 2,6-lutidine (6 ml) and 2-bromobutyraldehyde (5.5 g) (P. Duhamel, L. Duhamel, J-Y. Valnot, Bull. Soc. Chim. Fr. 1973(4) 1465) in xylene (200 ml) was heated under reflux overnight, removing water by means of a Dean and Stark apparatus. The reaction mixture was cooled, washed with dilute citric acid solution and the organic phase dried (Na2SO4) and concentrated. Column chromatography (SiO2, CH2Cl2) of the residue afforded the methyl ester of the title compound (4.6 g). A solution of the ester (4.6 g) in EtOH (100 ml) and 1N NaOH (50 mL) was heated under reflux for 3h. The reaction mixture was cooled, the EtOH evaporated and the aqueous residue washed with Et2O (50 mL). Acidification of the aqueous layer afforded the title compound (3.0 g).

Workup

  1. temperatureunder reflux overnight
  2. customremoving water by means of a Dean and Stark apparatus
  3. temperatureThe reaction mixture was cooled
  4. washwashed with dilute citric acid solution
  5. dry with materialthe organic phase dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9b10047a9b424a62b4354124a25f22a2
Source dataset
uspto-grants-1989_11
Patent number
US04882327

Reaction notes

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