Ethyl 2,4-dioxovalerate → HCID 178427252, compound

HRID 490315Notes

Reaction equation

HRID 490315 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:7])[NH:5][N:6]=1.C[O-].[Na+].C([O:13][C:14](=[O:21])[C:15](=O)[CH2:16][C:17](=O)[CH3:18])C>CO>[OH:7][C:4]1[C:3]2[C:2](=[N:1][C:15]([C:14]([OH:21])=[O:13])=[CH:16][C:17]=2[CH3:18])[NH:6][N:5]=1

Participants

5

Reactant 3

HCID 69208Ethyl 2,4-dioxovalerateHCID 962215-Amino-1H-pyrazol-3-olHCID 10942334Sodium Methoxide

Product 1

HCID 178427252HCID 178427252, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Amino-2H-pyrazol-3-ol (3.1 g, 31.6 mmol) were suspended in 100 ml of methanol. Then sodium methoxide (5.1 g, 95 mmol) and 2,4-dioxopentanoic acid ethyl ester (5 g, 31.6 mmol) were added, and the mixture was heated up under reflux for 12 h. The solvent was removed in a rotary evaporator, water was added to the residue, the precipitate was filtered off with suction, and the filtrate was adjusted to pH 6 with dilute hydrochloric acid. The precipitated product (both precipitates) was filtered off with suction and dried. Yield: 4.9 g (70%), M+H+: 194.09.

Workup

  1. temperaturethe mixture was heated up
  2. temperatureunder reflux for 12 h
  3. customThe solvent was removed in a rotary evaporator, water
  4. additionwas added to the residue
  5. filtrationthe precipitate was filtered off with suction
  6. customThe precipitated product (both precipitates)
  7. filtrationwas filtered off with suction
  8. customdried

Sources & evidence

ORD record
ord-914644e5cbc34774a7cd954f93d41aff
Source dataset
uspto-grants-2009_05
Patent number
US07528155B2

Reaction notes

Loading…