Acetic Anhydride → HCID 19068585, compound

HRID 1957089Notes

Reaction equation

HRID 1957089 reaction equation
O=[C:2]1[CH:7]=[CH:6][N:5]([CH:8]([CH2:18][CH3:19])[CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=[CH:3]1.[CH2:20]([O:28][C:29](=[O:33])[CH2:30][C:31]#[N:32])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(OC(=O)C)(=O)C>>[CH2:12]([C:11]1[CH:10]=[CH:9][C:8]([N:5]2[CH:4]=[CH:3][C:2](=[C:30]([C:29]([O:28][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:33])[C:31]#[N:32])[CH:7]=[CH:6]2)=[CH:18][CH:19]=1)[CH2:17][CH2:16][CH2:15][CH2:14][CH3:13]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 4384482Octyl cyanoacetateHCID 19068581HCID 19068581, compound

Product 1

HCID 19068585HCID 19068585, compound

Conditions

Temperature
140 °C

Procedure

In a 50 ml round bottom flask with stirbar, reflux condenser and nitrogen bubbler was placed the 4-(4-oxo-4Hpyridin-1-yl)hexylbenzene (0.638 g, 2.5 mmol), octylcyanoacetate (1.97 g, 10 mmol) and acetic anhydride (5.0 g). This mixture was heated in a 140° C. oil bath for 4.0 hours. After this period the mixture was cooled and crystalline product was isolated by suction filtration and washed well with acetic anhydride. The crude product was crystallized once from 1-propanol as yellow crystals (0.90 g, 83%).

Workup

  1. temperatureIn a 50 ml round bottom flask with stirbar, reflux condenser
  2. temperatureAfter this period the mixture was cooled
  3. customcrystalline product was isolated by suction filtration
  4. washwashed well with acetic anhydride
  5. customThe crude product was crystallized once from 1-propanol as yellow crystals (0.90 g, 83%)

Sources & evidence

ORD record
ord-a6a282ac537f400089c7b74d5c7b61f0
Source dataset
uspto-grants-1998_07
Patent number
US05783114

Reaction notes

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