Beta-Alanine → HCID 77519879, compound

HRID 965248Notes

Reaction equation

HRID 965248 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 (M--CH2)3Ph,18), 335(M-I,100), 327(M--NH(CH2), 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-a5c19977e4d14054bda2061bde625f37
Source dataset
uspto-grants-1998_06
Patent number
US05773476

Reaction notes

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