Ethyl 2-methylacetoacetate → HCID 23369854, compound

HRID 1900784Notes

Reaction equation

HRID 1900784 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH3:10])[CH:5]=[CH:4][C:3]=1[CH3:11].C(O[C:15](=O)[CH:16]([CH3:20])[C:17]([CH3:19])=[O:18])C.C(OCC)(=[O:24])C>CCCCCC>[CH2:9]([O:8][C:6]1[CH:5]=[CH:4][C:3]([CH3:11])=[C:2]([NH:1][C:19](=[O:24])[C:17](=[O:18])[CH:16]([CH3:20])[CH3:15])[CH:7]=1)[CH3:10]

Participants

5

Reactant 3

HCID 701Ethyl 2-methylacetoacetateHCID 8857Ethyl AcetateHCID 233697555-Ethoxy-2-methylaniline

Product 1

HCID 23369854HCID 23369854, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-amino-4-ethoxytoluene (590 mg, 3.99 mmol) and ethyl-2-methylacetoacetate (560 mg, 3.88 mmol) was stirred in a bath of 150° C. for 4 hours. The resultant mixture was subjected to silica gel column chromatography (developer: ethyl acetate--n-hexane), and the fraction containing the target substance was condensed, followed by recrystallizing from a solvent mixture of chloroform--n-hexane. As a result, 252 mg of the title compound was obtained as yellow powder (25.9%).

Workup

  1. additionthe fraction containing the target substance
  2. customcondensed
  3. customby recrystallizing from a solvent mixture of chloroform

Sources & evidence

ORD record
ord-36edbe23fd32437cb408b4f98e9b9bb7
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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