Beta-Alanine → HCID 77519879, compound

HRID 1351448Notes

Reaction equation

HRID 1351448 reaction equation
[CH3:1]OC1C=C(C=O)C=C(I)C=1O.[C:13]1([CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:27])[CH2:24][C:25]#[N:26])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.NCCC(O)=O>C(O)C>[C:13]1([CH2:19][CH2:20][CH2:21][NH:22][C:23]([C:24](=[CH2:1])[C:25]#[N:26])=[O:27])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 79499Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-HCID 42956972-cyano-N-(3-phenylpropyl)acetamide

Product 1

HCID 77519879HCID 77519879, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.69 g, of 5-iodo vaniline, 0.5 g N-3-phenyl-n-propyl cyanoacetamide and 50 mg β-alanine in 30 ml ethanol were refluxed 5 hours. Evaporation gave an oil which was triturated with benzene-hexane and filtered to give 3-(4-hydroxyl-3-iodo-5-methoxyphenyl-2[(3-phenyl-n-propyl)aminocarbonyl acrylnitrile as a bright yellow solid (0.82 g, 71% yield, mp—83° C.). (3-methoxy 4 hydroxy 5-iodo α-cis cinnamone (3′phenyl propane)amide). (Should be kept solid and protected from light. Material in solution, 2 weeks at room light deteriorated partially.), NMR CDCl3 δ 8.12(1H, S), 7.75(1H, d, J=2.0 Hz), 7.68(1H, d, J=2.0 Hz), 7.30–7.10(5H, m), 3.96(3H, S, OCH3), 3.45(2H, q, J=6.0 Hz), 2.70(2H, t, J=6.0 Hz), 1.95(2H, quin, J=6.0. Hz). MS—462(M+, 53), 357(K-CH2)3Ph, 18), 335(M-I, 100), 327(M-NH(CH2)3 Ph, 31), m/e.

Workup

  1. customEvaporation
  2. customgave an oil which
  3. customwas triturated with benzene-hexane
  4. filtrationfiltered

Sources & evidence

ORD record
ord-70ee0c5fdf7947a0aff335db675ef119
Source dataset
uspto-grants-2007_05
Patent number
US07217737B2

Reaction notes

Loading…