Hydrochloric Acid → HCID 54735931, compound

HRID 1781628Notes

Reaction equation

HRID 1781628 reaction equation
C[O:2][C:3](=O)[C:4]1[C:5](=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=1)[NH:6][C:7](=[O:18])[CH2:8][S:9]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10].[H-].[Na+].O.Cl>O1CCCC1>[Cl:23][C:20]1[CH:19]=[C:5]2[C:4]([C:3]([OH:2])=[C:8]([S:9]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:10])[C:7](=[O:18])[NH:6]2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24758Sodium hydrideHCID 22364770HCID 22364770, compound

Product 1

HCID 54735931HCID 54735931, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.0 g (2.73 mmol) of N-(benzylsulfinyl)acetyl-4-chloro-anthranilic acid methyl ester is placed in 10 ml of tetrahydrofuran at 0°, and 0.13 g (3 mmol) of sodium hydride dispersion in oil (55%) is added thereto. The mixture is then stirred for 15 minutes at 0° and for 2 hours at room temperature. Water is added and the reaction mixture is then adjusted to pH 2-3 with 1N hydrochloric acid and extracted with ethyl acetate. The organic phases are washed with water and brine, combined, dried with sodium sulfate, filtered and concentrated. Crystallisation of the crude product from ethyl acetate/petroleum ether yields 7-chloro-3-(benzylsulfinyl)-4-hydroxy-2(1H)-quinolone in the form of colourless crystals having a melting point of 234° (decomp.).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phases are washed with water and brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customCrystallisation of the crude product from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-54b0cf48149a479facc2b574676e1020
Source dataset
uspto-grants-1997_05
Patent number
US05633379

Reaction notes

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