Ethyl 4-chloroacetoacetate → HCID 69317496, compound

HRID 1393340Notes

Reaction equation

HRID 1393340 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1)(=[O:3])[NH2:2].Cl[CH2:15][C:16](=O)[CH2:17][C:18]([O:20]CC)=[O:19]>C(OCC)(=O)C>[CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[C:1]1[O:3][CH:15]=[C:16]([CH2:17][C:18]([OH:20])=[O:19])[N:2]=1

Participants

4

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 75245Naphthalene-2-carboxamide

Product 1

HCID 69317496HCID 69317496, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-carbamoylnaphthalene (2.64 g, 15.4 mmol) and ethyl 4-chloroacetoacetate (2.06 g, 12.5 mmol) was stirred at 160° C. for 1 hr. and then diluted with ethyl acetate (200 ml) at room temperature. The solution was washed with saturated sodium bicarbonate aqueous solution and brine in turn, and then dried. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=8−4) to give ethyl ester of [2-(2-naphthyl)oxazol-4-yl]acetic acid(459 mg, 13%) as yellow crystals.

Workup

  1. washThe solution was washed with saturated sodium bicarbonate aqueous solution and brine in turn
  2. customdried
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=8−4)

Sources & evidence

ORD record
ord-ecca0581c968451782f5dcd5bdbd2198
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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