tert-Butyl 3-aminocrotonate → HCID 18962971, compound

HRID 1707274Notes

Reaction equation

HRID 1707274 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=O)[C:7](=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)[C:8](=[O:10])[CH3:9].[NH2:22]/[C:23](/[CH3:32])=[CH:24]\[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>C(O)CCC>[C:8]([C:7]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[C:23]([CH3:32])[NH:22][C:6]=1[CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 12221517tert-Butyl 3-aminocrotonateHCID 54109537HCID 54109537, compound

Product 1

HCID 18962971HCID 18962971, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

24 g (79 mmol) 1-chloro-6-(3-nitrophenyl-methylene)-5,7-octanedione and 25 g (0.159 mol) tert-butyl β-amino-crotonate are boiled under reflux in 200 ml 1-butanol for 18 h. The mixture is filtered and concentrated, and the residue is chromatographed over silica gel with toluene/acetone=9/1. The title compound is obtained as a yellow oil. Yield: 19.7 g (57%).

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated
  3. customthe residue is chromatographed over silica gel with toluene/acetone=9/1

Sources & evidence

ORD record
ord-0c2af8a7d6094339afd40e8e523144ab
Source dataset
uspto-grants-1994_10
Patent number
US05352684

Reaction notes

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