Beta-Alanine → HCID 22753443, compound

HRID 2163324Notes

Reaction equation

HRID 2163324 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[C:18](=O)[C:17]=2[C:20]2[CH:25]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:23]([OH:30])=[C:22]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:21]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C(#N)[CH:36]([CH2:38][C:39]#[N:40])O.[NH2:42]CCC(O)=O.C(OC(=O)C)(=O)C>>[C:26]([C:24]1[CH:25]=[C:20]([C:17]2[C:18](=[C:38]([C:36]#[N:42])[C:39]#[N:40])[C:16]=2[C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:10]([OH:11])=[C:9]([C:12]([CH3:14])([CH3:13])[CH3:15])[CH:8]=2)[CH:21]=[C:22]([C:31]([CH3:34])([CH3:32])[CH3:33])[C:23]=1[OH:30])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 4

HCID 239Beta-AlanineHCID 7918Acetic AnhydrideHCID 13223939HCID 13223939, compoundHCID 212535622-Hydroxybutanedinitrile

Product 1

HCID 22753443HCID 22753443, compoundYield 540.8%

Procedure

A mixture of 1.00 g (2.17 mmol) of bis(3,5-di-tert-butyl-4-hydroxyphenyl)cyclopropenone 4, 0.29 g (4.3 mmol) of malonitrile and 0.02 g of β-alanine in 3.0 ml of freshly distilled acetic anhydride was heated to reflux with stirring for 20 min. A white precipitate formed in the reddish brown solution. The mixture was cooled to room temperature, and the precipitate was collected by filtration and recrystallized from benzene to give 0.62 g (56%) of 6a as pale yellow needles; mp 280-281°, (dec); ir (KBr) 3560(m), 2960-2860(m), 2213(m), 2197(m), 1850(w), 1595(m), 1490(s), 1470(m), 1450(w), 1410(s), 1370(s), 1360(s), 1310(s), 1255(s), 1240(m), 1200(w), 1100(m), 1025(w), 925(w), 900(w), 890(sh), 885(w), 780(w), 760(w), 675(2), 655(w), 595 cm-1 (w); nmr (CDCl3) δ1.52(s, 36HO), 5.98(s,2H), 7.91(s,4H); uv-visible λmax (methanol) 233 nm (log 4.40), 242(4.34), 252(4.29), 299(4.62), 313(4.57), 368(4.54), 396(sh) (4.44); only the longest wavelength absorptions will be shown for the uv-visible spectrum in nonpolar solvents, λmax (benzene) 381 nm, 400(sh); mass spectrum m/e 510.32500 (calc. 510.32462); Anal. Calcd. for C34H42N2O2 : C, 79.95; H, 8.29; N, 5.49. Found: C, 80.03; H, 8.32; N, 5.43.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customA white precipitate formed in the reddish brown solution
  4. filtrationthe precipitate was collected by filtration
  5. customrecrystallized from benzene

Sources & evidence

ORD record
ord-0bab79b2b4d24c38b7de00658ecd61bd
Source dataset
uspto-grants-1979_01
Patent number
US04133821

Reaction notes

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