Acetic Anhydride → HCID 15029615, compound

HRID 893084Notes

Reaction equation

HRID 893084 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1/[CH:12]=[CH:13]/[NH:14][CH:15]=[O:16].[C:17](OC(=O)C)(=[O:19])[CH3:18]>N1C=CC=CC=1>[CH:15]([NH:14]/[CH:13]=[CH:12]/[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[O:1][C:17](=[O:19])[CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10130564HCID 10130564, compound

Product 1

HCID 15029615HCID 15029615, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cooled solution of (E)-N-[2-(2-hydroxynaphth-1-yl) ethenyl] formamide (2133 mg, 10 mmol) in dry pyridine (5 ml) is added acetic anhydride (2042 mg, 20 mmol) and the mixture maintained at 0°-5° overnight. Thereupon the mixture is concentrated under vacuum, the residue dissolved in dichloromethane, the organic layer washed with water and then evaporated under reduced pressure. The crude product is crystallized from chloroform/methanol to yield pure title compound in 90% yield (2300 mg).

Workup

  1. temperaturethe mixture maintained at 0°-5° overnight
  2. concentrationThereupon the mixture is 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 is crystallized from chloroform/methanol

Sources & evidence

ORD record
ord-52ec1ae1f35a4170b2cf8ce8494aa260
Source dataset
uspto-grants-1992_06
Patent number
US05122537

Reaction notes

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