Acetic Acid → HCID 86638785, compound

HRID 1618877Notes

Reaction equation

HRID 1618877 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]([OH:12])([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[C:14](#[N:18])[CH2:15][C:16]#[N:17].C(O)(=O)C.[N:23]1C=C[CH:26]=[CH:25][CH:24]=1>>[C:24]([C:25]1[C:26](=[C:15]([C:14]#[N:18])[C:16]#[N:17])[O:12][C:9]([CH3:11])([CH3:10])[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)#[N:23]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 8010MalononitrileHCID 54135387612070-27-6

Product 1

HCID 86638785HCID 86638785, compound

Procedure

A mixture of the crude liquid 1-(4-bromophenyl)-2-hydroxy-2-methyl-propan-1-one (28.0 g, 65% 115 mmol, 74 mmol), malononitrile (35 g, 0.52 mol), acetic acid (0.4 g) and dry pyridine (100 mL) was stirred at room temperature for 24 hrs. The reaction mixture was then poured into 1 L of ice water with vigorous stirring and kept in the refrigerator overnight. The yellow precipitate was collected by vacuum filtration, washed with methanol and dried under vacuum. The product was recrystallized from 70% dichloromethane/methanol. Yield: 10.0 g (40%). mp: 235° C. 1H NMR (400 MHz, CDCl3) δ 1.77 (s, 6H),) 7.58 (d, J=8.4 Hz, 2H), 7.72 (d, J=8.4 Hz, 2H). 13C NMR (100 MHz, (100 MHz, CDCl3) δ 176.55, 174.76, 133.35, 129.40, 129.18 125.89, 111.05, 110.19, 110.05, 99.21, 26.09.

Workup

  1. stirringwith vigorous stirring
  2. customkept in the refrigerator overnight
  3. filtrationThe yellow precipitate was collected by vacuum filtration
  4. washwashed with methanol
  5. customdried under vacuum
  6. customThe product was recrystallized from 70% dichloromethane/methanol

Sources & evidence

ORD record
ord-998a02f5731a45c593f2e94df9235cfe
Source dataset
uspto-grants-2014_07
Patent number
US08772048B2

Reaction notes

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