4-Amino-3-penten-2-one → HCID 18962993, compound

HRID 1707280Notes

Reaction equation

HRID 1707280 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=O)[C:9](=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1)[C:10](=[O:12])[CH3:11].[NH2:24][C:25](=[CH:27][C:28](=[O:30])[CH3:29])[CH3:26]>CO>[C:10]([C:9]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:27]([C:28](=[O:30])[CH3:29])=[C:25]([CH3:26])[NH:24][C:8]=1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 1368734-Amino-3-penten-2-oneHCID 54361291HCID 54361291, compound

Product 1

HCID 18962993HCID 18962993, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

45 g (0.14 mol) 1-bromo-8-(3-nitrophenyl-methylene)-7,9-decanedione and 28 g (0.28 mol) 2-amino-2-penten-4-one are boiled under reflux in 300 ml methanol for 24 h. The mixture is concentrated and the residue is prepurified by chromatography with toluene/acetone=99/1. The product thus obtained is chromatographed again over silica gel with toluene/ethyl acetate=8/2The title compound is obtained as a yellow oil. Yield: 10.3 g (16%).

Workup

  1. concentrationThe mixture is concentrated
  2. customThe product thus obtained
  3. customis chromatographed again over silica gel with toluene/ethyl acetate=8/2The title compound
  4. customis obtained as a yellow oil

Sources & evidence

ORD record
ord-de726593acef4dbbbd78e66dbeaea53b
Source dataset
uspto-grants-1994_10
Patent number
US05352684

Reaction notes

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