Acetic Anhydride → HCID 21936635, compound

HRID 1241720Notes

Reaction equation

HRID 1241720 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[C:12]([CH2:20][CH2:21][CH:22]([OH:29])[C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[C:11]2=[O:30])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:31](OC(=O)C)(=[O:33])[CH3:32]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[C:12]([CH2:20][CH2:21][CH:22]([O:29][C:31](=[O:33])[CH3:32])[C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)[C:11]2=[O:30])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 21936644HCID 21936644, compound

Product 1

HCID 21936635HCID 21936635, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(3-nitrophenyl)-3-[3-hydroxy-3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one (50 mg, 0.12 mmol; prepared in Example 20) in acetic anhydride (0.2 ml) and pyridine (0.3 ml) was heated at 100° C. for 20 min, concentrated, and extracted with chloroform. The extract was treated according to conventional techniques, concentrated, and then purified by flash column chromatography to afford 1-(3-nitrophenyl)-3-[3-acetyloxy-3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one (55.2 mg, 100%; mp 69–71° C.).

Workup

  1. concentrationconcentrated
  2. extractionextracted with chloroform
  3. additionThe extract was treated
  4. concentrationconcentrated
  5. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-6147352068f74fabaf8b055cf2fe14e4
Source dataset
uspto-grants-2006_10
Patent number
US07115623B2

Reaction notes

Loading…