Acetic Anhydride → HCID 54564406, compound

HRID 266703Notes

Reaction equation

HRID 266703 reaction equation
[C:1]1([NH:7][C:8](=[O:24])[C:9]([C:22]#[N:23])=[CH:10][C:11]2[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:14]([OH:21])=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>N1C=CC=CC=1>[C:1]1([NH:7][C:8](=[O:24])[C:9]([C:22]#[N:23])=[CH:10][C:11]2[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:14]([O:21][C:25](=[O:27])[CH3:26])=[CH:13][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54527172HCID 54527172, compound

Product 1

HCID 54564406HCID 54564406, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cooled solution of N-phenyl β-(4-hydroxy-5,6,7,8-tetrahydronaphth-1-yl)-α-cyanoacrylamide (3.184 g, 0.010 mol) in dry pyridine (5 ml) was added acetic anhydride (2.040 g, 0.020 mol) and the mixture maintained at 0°-5° C. overnight. Thereupon the mixture was concentrated under vacuum, the residue dissolved in dichloromethane, the organic layer washed with water and then evaporated under reduced pressure. The crude product was crystallized from chloroform/methanol to yield pure title compound in about 80% yield.

Workup

  1. temperaturethe mixture maintained at 0°-5° C. overnight
  2. concentrationThereupon the mixture was concentrated under vacuum
  3. dissolutionthe residue dissolved in dichloromethane
  4. washthe organic layer washed with water
  5. customevaporated under reduced pressure
  6. customThe crude product was crystallized from chloroform/methanol

Sources & evidence

ORD record
ord-ab19fcfc082c40c3a3a4d157484b18d1
Source dataset
uspto-grants-1997_07
Patent number
US05652250

Reaction notes

Loading…