Ethyl 2-methylacetoacetate → HCID 85611941, compound

HRID 844437Notes

Reaction equation

HRID 844437 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[N:10]([O-])=O.[Na+].[CH3:14][CH:15](C(=O)C)[C:16]([O:18][CH2:19][CH3:20])=[O:17].[OH-].[K+]>Cl.O.C(O)C>[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH:4][N:10]=[C:15]([CH3:14])[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

8

Reactant 4

HCID 701Ethyl 2-methylacetoacetateHCID 72502,4-DimethylanilineHCID 14797Potassium HydroxideHCID 23668193Sodium Nitrite

Product 1

HCID 85611941HCID 85611941, compoundYield 77.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolventHCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

17.11 g of 2,4-dimethylaniline are dissolved in 36 ml of concentrated HCl diluted with 280 ml of water. A solution of 10.13 g of sodium nitrite in 30 ml of water is added, at 0° C. This mixture is stirred for 15 minutes at 0° C. and the solution obtained is then poured, at 0° C., onto a solution of 20.5 g of ethyl 2-methyl-3-oxobutyrate in 150 ml of ethanol. At the same time, 31.7 g of potassium hydroxide dissolved in 32 ml of water are added and the mixture is then stirred for 15 minutes at 0° C. The medium is neutralized with 70.6 ml of 2N HCl. The precipitate formed is filtered off, washed with water and then dissolved in EtOAc. This solution is dried over Na2SO4 and concentrated. The crystalline residue is taken up in isopropyl ether and then filtered to give 25.49 g of the expected compound: m.p.=146° C.

Workup

  1. customthe solution obtained
  2. additionare added
  3. stirringthe mixture is then stirred for 15 minutes at 0° C
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washwashed with water
  7. dissolutiondissolved in EtOAc
  8. dry with materialThis solution is dried over Na2SO4
  9. concentrationconcentrated
  10. filtrationfiltered

Sources & evidence

ORD record
ord-4aa441f8b5c54021980bd0f97afc5427
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Reaction notes

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