Benzylamine → 5-(2,2-Dicyanoethenyl)-2-hydroxybenzoic acid

HRID 421049Notes

Reaction equation

HRID 421049 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[CH:6]([C:8]1[CH:16]=[C:12]([C:13]([OH:15])=[O:14])[C:11]([OH:17])=[CH:10][CH:9]=1)=O.C(N)C1C=CC=CC=1>C(O)C>[C:3]([C:2]([C:1]#[N:5])=[CH:6][C:8]1[CH:9]=[CH:10][C:11]([OH:17])=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14])#[N:4]

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8010MalononitrileHCID 692265-Formylsalicylic acid

Product 1

HCID 157071045-(2,2-Dicyanoethenyl)-2-hydroxybenzoic acidYield 32.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Malononitrile (132 mg, 2 mmol) was dissolved in ethanol (6 mL), and 5-formylsalicylic acid (332 mg, 2 mmol) was added. After cooling with ice bath, benzylamine (0.1 mL) was added and the mixture was stirred at room temperature for 2 hours. The separated yellow crystal was filtered and recrystallized (ethanol) to give the title compound (139.9 mg, 32.7%) as a light yellow solid.

Workup

  1. temperatureAfter cooling with ice bath
  2. filtrationThe separated yellow crystal was filtered
  3. customrecrystallized (ethanol)

Sources & evidence

ORD record
ord-25a1ee5930f244618665a8a2cb26938e
Source dataset
uspto-grants-2012_01
Patent number
US08097759B2

Reaction notes

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