Methyl acetoacetate → HCID 13505726, compound

HRID 1981537Notes

Reaction equation

HRID 1981537 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH:5]=O)=[CH2:2].[NH2:13]/[C:14](/[CH3:20])=[CH:15]\[C:16]([O:18][CH3:19])=[O:17].[C:21]([O:27][CH3:28])(=[O:26])[CH2:22][C:23]([CH3:25])=O.[OH-].[NH4+]>CO>[CH3:20][C:14]1[NH:13][C:23]([CH3:25])=[C:22]([C:21]([O:27][CH3:28])=[O:26])[CH:5]([C:4]2[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:3]=2[CH:1]=[CH2:2])[C:15]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 14923Ammonium HydroxideHCID 643918Methyl 3-aminocrotonateHCID 13505725HCID 13505725, compound

Product 1

HCID 13505726HCID 13505726, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To compound (3d) (8.0 g, 49.3 mmol) in anhydrous methanol (50 ml) was added methyl 3-aminocrotonate (5.68 g, 49.3 mmol), methyl acetoacetate (5.72 g, 49.3 mmol), and concentrated ammonium hydroxide (1 ml) and the resulting solution heated at reflux under nitrogen for 4 days. The solvent was removed in vacuo and the residual material triturated with ether (20 ml) to give compound (3e) as a pale, yellowish solid, mp 141°-143°.

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux under nitrogen for 4 days
  3. customThe solvent was removed in vacuo
  4. customthe residual material triturated with ether (20 ml)

Sources & evidence

ORD record
ord-776cab52493548ec8c44388925745af0
Source dataset
uspto-grants-1986_06
Patent number
US04593033

Reaction notes

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