Methyl acetoacetate → HCID 15170334, compound

HRID 2372825Notes

Reaction equation

HRID 2372825 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][CH:13]=[C:14]([CH:17]=O)[C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19]([O:25][CH3:26])(=[O:24])[CH2:20][C:21]([CH3:23])=O.[NH2:27]/[C:28](/[CH3:32])=[CH:29]\[C:30]#[N:31]>C(O)C>[CH3:23][C:21]1[NH:27][C:28]([CH3:32])=[C:29]([C:30]#[N:31])[CH:17]([C:14]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:15]=2[CH:16]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[N:9]3)[C:20]=1[C:19]([O:25][CH3:26])=[O:24]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 151703323-Phenylquinoline-5-carbaldehyde

Product 1

HCID 15170334HCID 15170334, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.7 g (3 mmol) of 3-phenylquinoline-5-aldehyde in 6 ml of ethanol are boiled with 0.35 g (3 mmol) of methyl acetoacetate and 0.25 g (3 mmol) of 3-aminocrotononitrile for 24 hours. The mixture is cooled and concentrated. The evaporation residue is purified by means of a silica gel column using toluene/ethyl acetate mixtures. The clean fractions are combined and concentrated. 0.5 g of colorless substance of melting point 242° C. are obtained by crystallization from isopropanol.

Workup

  1. temperatureThe mixture is cooled
  2. concentrationconcentrated
  3. customThe evaporation residue is purified by means of a silica gel column
  4. concentrationconcentrated
  5. custom0.5 g of colorless substance of melting point 242° C. are obtained by crystallization from isopropanol

Sources & evidence

ORD record
ord-e1b2ebd3e8f142a5bd360630a948d013
Source dataset
uspto-grants-1992_03
Patent number
US05100900

Reaction notes

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