Acetic Anhydride → HCID 15044008, compound

HRID 1769642Notes

Reaction equation

HRID 1769642 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N+:9]([O-])=[C:10]3[C:15]=1[C:14](=[O:16])[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[C:18]([O:21]C(=O)C)(=[O:20])[CH3:19]>>[C:18]([O:21][CH:11]1[C:10]2[C:15](=[C:2]([NH2:1])[C:3]3[C:8]([N:9]=2)=[CH:7][CH:6]=[CH:5][CH:4]=3)[C:14](=[O:16])[CH2:13][CH2:12]1)(=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 178507165HCID 178507165, compound

Product 1

HCID 15044008HCID 15044008, compoundYield 52%

Procedure

A solution of 9-amino-3,4-dihydroacridin-1(2H)-one N-oxide (5.4 g) and acetic anhydride (60 ml) was heated to reflux and then concentrated. The residue was stirred in saturated sodium bicarbonate solution for one hr. The mixture was filtered and the filter cake was washed with water and dried under vacuum at 40° C. for three hrs to yield 1.93 g of product, mp 208° C. (dec). An additional 1.38 g, mp 208° C. (dec), of product was obtained by extraction of the tiltrate with ethyl acetate, evaporation of ethyl acetate extract, and trituration of the residue with diethyl ether; total 52% yield.

Workup

  1. temperatureto reflux
  2. concentrationconcentrated
  3. filtrationThe mixture was filtered
  4. washthe filter cake was washed with water
  5. customdried under vacuum at 40° C. for three hrs

Sources & evidence

ORD record
ord-3e17ab538baa4ea69a93a016a295dfb3
Source dataset
uspto-grants-1995_01
Patent number
US05382594

Reaction notes

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