Isopropyl acetoacetate → HCID 20077494, compound

HRID 2379704Notes

Reaction equation

HRID 2379704 reaction equation
[C:1]1([C:7]2[N: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.[NH2:19]/[C:20](/[CH3:24])=[CH:21]\[C:22]#[N:23].[C:25]([O:31][CH:32]([CH3:34])[CH3:33])(=[O:30])[CH2:26][C:27]([CH3:29])=O>C(O)C>[C:22]([C:21]1[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:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[N:9]3)[C:26]([C:25]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])=[C:27]([CH3:29])[NH:19][C:20]=1[CH3:24])#[N:23]

Participants

5

Reactant 3

HCID 68329Isopropyl acetoacetateHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 20077497HCID 20077497, compound

Product 1

HCID 20077494HCID 20077494, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

750 mg (3.2 mmol) of 3-phenyl-5-cinnolinecarboxaldehyde, 263 mg (3.2 mmol) of 3-aminocrotononitrile and 457 mg (3.2 mmol) of isopropyl acetoacetate are boiled under reflux for 2.5 days in 25 ml of ethanol. The mixture is concentrated and separated on a silica gel column using toluene/ethyl acetate mixtures. The desired fractions are collected and concentrated. The evaporation residue obtained is crystallised using ether and filtered off with suction. 320 mg of crystals of melting point 200°-202° C. are obtained.

Workup

  1. concentrationThe mixture is concentrated
  2. customseparated on a silica gel column
  3. customThe desired fractions are collected
  4. concentrationconcentrated
  5. customThe evaporation residue obtained
  6. customis crystallised
  7. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-948d04af4be14806a7c4e331696a0554
Source dataset
uspto-grants-1994_11
Patent number
US05364855

Reaction notes

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