Acetyl chloride → HCID 135997572, compound

HRID 1175823Notes

Reaction equation

HRID 1175823 reaction equation
[C:1](Cl)(=O)C.[NH2:5][C:6]1[N:7]([C:25]2[CH:30]=[C:29]([OH:31])[C:28]([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:27][C:26]=2[CH3:39])[N:8]=[C:9]2[C:18]3[CH:17]=[CH:16][C:15]([O:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:14][C:13]=3[NH:12][C:11](=[O:24])[C:10]=12.C(=O)([O-])O.[Na+]>CO>[CH3:1][O:22][C:21](=[O:23])[CH2:20][O:19][C:15]1[CH:16]=[CH:17][C:18]2[C:9]3[C:10](=[C:6]([NH2:5])[N:7]([C:25]4[CH:30]=[C:29]([OH:31])[C:28]([O:32][C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=5)=[CH:27][C:26]=4[CH3:39])[N:8]=3)[C:11](=[O:24])[NH:12][C:13]=2[CH:14]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 135599945HCID 135599945, compound

Product 1

HCID 135997572HCID 135997572, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of acetyl chloride (2 ml) and methanol (20 ml) was added {[3-amino-2-(5-hydroxy-2-methyl-4-phenoxyphenyl)-4-oxo-4,5-dihydro-2H-pyrazolo[4,3-c]quinolin-7-yl]oxy}acetic acid (145 mg). The mixture was heated under reflux with stiring for one night. The reaction mixture was cooled, a 5% aqueous sodium hydrogen carbonate solution was added thereto, and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. To the residue was added ethyl acetate-hexane, the precipitated solid was collected by filtration, washed with ethyl acetate-hexane to obtain the target compound (130 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. waitwith stiring for one night
  4. temperatureThe reaction mixture was cooled
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionTo the residue was added ethyl acetate-hexane
  10. filtrationthe precipitated solid was collected by filtration
  11. washwashed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-3c9b602f91fa40799ec25331f1fab133
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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