Methyl 4-chloroacetoacetate → HCID 16413490, compound

HRID 2099017Notes

Reaction equation

HRID 2099017 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[CH3:9][O:10][C:11](=[O:17])[CH2:12][C:13](=O)[CH2:14]Cl>C1(C)C=CC=CC=1>[CH3:9][O:10][C:11](=[O:17])[CH2:12][C:13]1[N:1]=[C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]2[CH:14]=1

Participants

4

Reactant 2

HCID 36240Methyl 4-chloroacetoacetateHCID 661742-Amino-5-chloropyridine

Product 1

HCID 16413490HCID 16413490, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.28 g (10 mmol) 2-Amino-5-chloropyridine and 1.18 mL (1 eq) 4-chloro-3-oxo-butyric acid methyl ester are heated to 115° C. in 15 mL toluene for 18 h. The resulting brown suspension is evaporated and heated 1 h to 90° C. under high vacuum, then cooled to room temperature and stirred in 100 mL dichloromethane, 10 mL saturated aqueous sodium bicarbonate solution and 40 mL water at 0° C. for one hour. The organic phase is then separated and evaporated to yield a brownish solid that is column chromatographed (silica gel, ethyl acetate/petroleum ether 4:1) to yield 700 mg (31 %) desired product as a beige powder. MS(EI+): 225-227 (M+1).

Workup

  1. customThe resulting brown suspension is evaporated
  2. temperatureheated 1 h to 90° C. under high vacuum
  3. customThe organic phase is then separated
  4. customevaporated
  5. customto yield a brownish solid
  6. customchromatographed (silica gel, ethyl acetate/petroleum ether 4:1)

Sources & evidence

ORD record
ord-39f8254b148440e5a54cc71bd189ff02
Source dataset
uspto-grants-2009_08
Patent number
US07569337B2

Reaction notes

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