Hydrochloric Acid → HCID 22054464, compound

HRID 1829704Notes

Reaction equation

HRID 1829704 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N:12]2[C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:22])[C:16]=3[C:15]3=[N:23][O:24][C:25]([CH3:26])=[C:14]3[C:13]2=[O:27])[N:7]=1)C.CO.[OH-].[Na+].Cl>O.C1COCC1>[Cl:22][C:17]1[C:16]2[C:15]3[C:14](=[C:25]([CH3:26])[O:24][N:23]=3)[C:13](=[O:27])[N:12]([C:8]3[N:7]=[C:6]([CH2:5][C:4]([OH:28])=[O:3])[CH:11]=[CH:10][CH:9]=3)[C:21]=2[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 9930712HCID 9930712, compound

Product 1

HCID 22054464HCID 22054464, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Heat [6-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-pyridin-2-yl]-acetic acid ethyl ester (0.359 g, 0.9 mmol), MeOH (4.5 ml), THF (0.5ml), and 1N NaOH (1.8 ml, 1.8 mmol) at 50° C. for 2 h. Cool to room temperature, dilute with H2O, and acidify (conc. HCl) to less than pH 3. Extract with EtOAc twice and wash the combined extracts (H2O then brine), dry (MgSO4), filter, and concentrate giving the title compound (0.338 g, 100%). Use this material without further purification. Mass Spectrum (FIA) (m/z) 370.0 [M+1]

Workup

  1. extractionExtract with EtOAc twice
  2. washwash the combined extracts (H2O
  3. dry with materialbrine), dry (MgSO4)
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-603e300b4e31415eab1a0a050b9243b0
Source dataset
uspto-grants-2006_06
Patent number
US07064131B2

Reaction notes

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