Ethyl Acetoacetate → HCID 178429256, compound

HRID 417998Notes

Reaction equation

HRID 417998 reaction equation
Cl.[C:2]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][NH2:13])=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[C:14](OCC)(=[O:19])[CH2:15][C:16]([CH3:18])=O>C(O)(=O)C>[C:2]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[C:14]([OH:19])=[CH:15][C:16]([CH3:18])=[N:13]2)=[CH:10][CH:11]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 162174584-Tert-butylphenylhydrazine hydrochloride

Product 1

HCID 178429256HCID 178429256, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-t-Butylphenylhydrazine hydrochloride (24.2 g, 120 mmol) in acetic acid (600 mL) was stirred with ethyl acetoacetate (16.4 mL, 129 mmol) at 100° C. for 22 hours. The solvent was removed by distillation under reduced pressure, and the resulting solid was recrystallized from chloroform (70 ml, 40° C.)-diethyl ether (200 mL, 0° C.), washed with diethyl ether and dried under reduced pressure to give 21.7 g of the desired product (78% yield).

Workup

  1. customThe solvent was removed by distillation under reduced pressure
  2. customthe resulting solid was recrystallized from chloroform (70 ml, 40° C.)-diethyl ether (200 mL, 0° C.)
  3. washwashed with diethyl ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-49cecee3fe5b43ebac7700385081b591
Source dataset
uspto-grants-2012_01
Patent number
US08093251B2

Reaction notes

Loading…