Beta-Alanine → 2-[(6-nitro-2H-1,3-benzodioxol-5-yl)methylidene]propanedinitrile

HRID 895953

Reaction equation

HRID 895953 reaction equation
[CH2:1]1[O:11][C:10]2[CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]([CH:6]=O)=[CH:4][C:3]=2[O:2]1.[C:15](#[N:19])[CH2:16][C:17]#[N:18].NCCC(O)=O.O>C(O)C>[CH2:1]1[O:11][C:10]2[CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]([CH:6]=[C:16]([C:15]#[N:19])[C:17]#[N:18])=[CH:4][C:3]=2[O:2]1

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 962WaterHCID 8010MalononitrileHCID 128406-Nitro-1,3-benzodioxole-5-carboxaldehyde

Product 1

HCID 7079142-[(6-nitro-2H-1,3-benzodioxol-5-yl)methylidene]propanedinitrileYield 80.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 g (5.1 mmol) 3,4-Methylenedioxy-6-nitrobenzaldehyde, 0.4 g (6 mmol) malononitrile and 0.2 g β-alanine in 30 ml ethanol were stirred 16 hours at room temperature, 50 ml H2O was added and the reaction mixture was filtered, giving 1 g (80% yield) of a bright yellow solid, m.p. 104° C.

Workup

  1. filtrationthe reaction mixture was filtered

Sources & evidence

ORD record
ord-a91411fcbc114066b6c3c11805a2e5e1
Source dataset
uspto-grants-2005_07
Patent number
USRE038761E1

Linked notes

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