2-Chloroethyl acetoacetate → HCID 14578930, compound

HRID 231817Notes

Reaction equation

HRID 231817 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][CH:3]=1.[C:10]([O:16][CH2:17][CH2:18][Cl:19])(=[O:15])[CH2:11][C:12]([CH3:14])=O.[NH2:20]/[C:21](/[CH3:27])=[CH:22]\[C:23]([O:25][CH3:26])=[O:24]>C(O)(C)C>[CH3:26][O:25][C:23]([C:22]1[CH:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=2)[C:11]([C:10]([O:16][CH2:17][CH2:18][Cl:19])=[O:15])=[C:12]([CH3:14])[NH:20][C:21]=1[CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 1086052-Chloroethyl acetoacetateHCID 643918Methyl 3-aminocrotonateHCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 14578930HCID 14578930, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 6-bromo-2-pyridine aldehyde (1.542 g, 8.29 mmol), chloroethyl acetoacetate (1.388 g, 8.43 mmol) and methyl 3-aminocrotonate (948 mg, 8.29 mmol) in 12 ml of isopropanol was stirred under a nitrogen gas stream, at 40° C. for 9 hours and at room temperature for 13 hours. The reaction solvent was distilled off under reduced pressure, and the residue was purified by column chromatography [silica gel; ethyl acetate-n-hexane (2:3)]. The crude product thus obtained was recrystallized from isopropyl ether-methanol to obtain 1.730 g (49% yield) of the above-captioned compound (m.p. 152° to 153°C.).

Workup

  1. waitat room temperature for 13 hours
  2. distillationThe reaction solvent was distilled off under reduced pressure
  3. customthe residue was purified by column chromatography [silica gel; ethyl acetate-n-hexane (2:3)]
  4. customThe crude product thus obtained
  5. customwas recrystallized from isopropyl ether-methanol

Sources & evidence

ORD record
ord-73a55dd289d240c091c881148f447e98
Source dataset
uspto-grants-1989_07
Patent number
US04849429

Reaction notes

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