Water → HCID 22718465, compound

HRID 1582654Notes

Reaction equation

HRID 1582654 reaction equation
Cl.[NH2:2][CH2:3][C:4](=O)[CH:5]([CH3:7])[CH3:6].[C:9](OCC)(=O)[CH2:10][C:11]([CH3:13])=O.[C:18]([O-:21])(=O)[CH3:19].[Na+].[OH2:23]>C(O)(=O)C>[CH:5]([C:4]1[C:10]([C:9]([O:21][CH2:18][CH3:19])=[O:23])=[C:11]([CH3:13])[NH:2][CH:3]=1)([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8868Ethyl AcetoacetateHCID 517045Sodium AcetateHCID 134017361-Amino-3-methylbutan-2-one hydrochloride

Product 1

HCID 22718465HCID 22718465, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution containing 0.32 g of 4-amino-2-methyl-3-butanone hydrochloride, 0.33 g of ethyl acetoacetate and 0.28 g of sodium acetate in 2 ml of 75% acetic acid was heated at 100° C. for 1.5 h. The mixture was poured into 10 ml of water and extracted three times with 10 ml of diethyl ether. Combined extracts were washed three times with 10 ml of saturated sodium hydrogen carbonate and with 10 ml of brine then dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using dichloromethane for the elution to give 0.15 g of ethyl 4-isopropyl-2-methyl-1H-pyrrole-3-carboxylate. Recrystallisation from isohexane gave analytically pure material of melting point 67-68.5° C.; mass spectrum (EI) m/z 195 [M]+.

Workup

  1. extractionextracted three times with 10 ml of diethyl ether
  2. washCombined extracts were washed three times with 10 ml of saturated sodium hydrogen carbonate
  3. dry with materialwith 10 ml of brine then dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-0e63c2b6c2274ac08f9a58d8b69a2c5d
Source dataset
uspto-grants-2004_05
Patent number
US06737429B2

Reaction notes

Loading…