Acetic Anhydride → HCID 23154093, compound

HRID 1175796Notes

Reaction equation

HRID 1175796 reaction equation
[NH2:1][C:2]1[N:3]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][OH:33])=[CH:27][CH:26]=2)[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:7](=[O:24])[C:6]=12.[C:34](OC(=O)C)(=[O:36])[CH3:35]>>[OH:33][CH2:32][CH2:31][C:28]1[CH:27]=[CH:26][C:25]([N:3]2[C:2]([NH:1][C:34](=[O:36])[CH3:35])=[C:6]3[C:7](=[O:24])[N:8]([CH2:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[C:5]3=[N:4]2)=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 23153827HCID 23153827, compound

Product 1

HCID 23154093HCID 23154093, compound

Procedure

A mixture of 3-amino-2-[4-(2-hydroxyethyl)phenyl]-5-(4-methoxybenzyl)-2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one (0.2 g) and acetic anhydride (2 ml) was heated under reflux for 5 hours. The reaction mixture was concentrated under reduced pressure, an aqueous sodium hydrogen carbonate solution was added thereto, and extracted with ethyl acetate. The extract was washed with water and saturated brine, and concentrated after drying. To the obtained crystal was added methanol (20 ml) and an 1N aqueous sodium hydroxide solution (0.5 ml), and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure, a 1N hydrochloric acid (0.5 ml) was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with an aqueous sodium hydrogen carbonate solution, water and saturated brine, dried and concentrated to obtain the target compound (0.2 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionan aqueous sodium hydrogen carbonate solution was added
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water and saturated brine
  7. concentrationconcentrated
  8. customafter drying
  9. additionTo the obtained crystal was added methanol (20 ml)
  10. distillationThe solvent was distilled off under reduced pressure
  11. additiona 1N hydrochloric acid (0.5 ml) was added to the residue
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe extract was washed with an aqueous sodium hydrogen carbonate solution, water and saturated brine
  14. customdried
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-470eebc82ac34c25a653c1964a91200b
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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