Acetic Anhydride → HCID 14639188, compound

HRID 1460144Notes

Reaction equation

HRID 1460144 reaction equation
[C:1]1([C:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10](=[O:17])[N:9]3[CH2:18][CH2:19][NH:20][C:8]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([N:20]1[C:8]2[N:9]([C:10](=[O:17])[C:11]3[CH:12]=[CH:13][CH:14]=[N:15][C:16]=3[C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:18][CH2:19]1)(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 14639175HCID 14639175, compound

Product 1

HCID 14639188HCID 14639188, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Reflux a mixture of 2,3-dihydro-10-phenylimidazo-[1,2-g][1,6]naphthyridin-5(1H)-one (5.5 g), acetic anhydride (10 ml), and pyridine (60 ml) for 30 hours. Cool the reaction mixture and evaporate the volatile reagents--i.e., excess pyridine and acetic anhydride. Partition the residue between chloroform and water, and dry, filter, and concentrate the organic solution Chromatograph the residue over silica gel, elute the column with chloroform, and crystallize the eluate from chloroform-petroleum ether to obtain 1-acetyl-2,3-dihydro-10-phenyl-imidazo[1,2-g][1,6]naphthyridin-5(1H)-one, mp 229°-231° C.

Workup

  1. temperatureReflux
  2. temperatureCool the reaction mixture
  3. customevaporate the volatile reagents
  4. customPartition the residue between chloroform and water
  5. customdry
  6. filtrationfilter
  7. concentrationconcentrate the organic solution Chromatograph the residue over silica gel
  8. washelute the column with chloroform
  9. customcrystallize the eluate from chloroform-petroleum ether

Sources & evidence

ORD record
ord-d079b1e1554b446c9d90b3c5084dffd2
Source dataset
uspto-grants-1991_12
Patent number
US05070086

Reaction notes

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