6-Methoxypyridine-3-carbaldehyde → HCID 53930754, compound

HRID 127193

Reaction equation

HRID 127193 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=O)=[CH:5][CH:4]=1.[C:11]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:12]C([O-])=O>N1CCCCC1.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=[CH:12][C:11]([O:17][CH2:18][CH3:19])=[O:16])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 33645766-Methoxypyridine-3-carbaldehydeHCID 3595298Propanedioic acid, monoethyl ester

Product 1

HCID 53930754HCID 53930754, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 6-methoxypyridine-3-carboxaldehyde (2.34 g), monoethyl malonate (4.51 g), pyridine (12 ml) and piperidine (6 drops) was heated under reflux for 5 hours and was evaporated to an oil. This oil was partitioned between ether and dilute aqueous ammonia. The ether layer was washed with water and evaporated to an oil which crystallised on standing to give ethyl 3-(6-methoxy-3-pyridyl)acrylate (2.8 g, 79%), m.p. 49-52°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customwas evaporated to an oil
  4. customThis oil was partitioned between ether and dilute aqueous ammonia
  5. washThe ether layer was washed with water
  6. customevaporated to an oil which
  7. customcrystallised

Sources & evidence

ORD record
ord-0e168bd7f1a34e58b18e711c954c5def
Source dataset
uspto-grants-1981_03
Patent number
US04255428

Linked notes

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