Hydrochloric Acid → HCID 135528948, compound

HRID 1954174Notes

Reaction equation

HRID 1954174 reaction equation
COC[O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[C:9]([C:16]1[N:17]=[N:18][N:19]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]4[CH:39]=[CH:38][C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[N:31]=4)[CH:23]=3)[N:20]=1)=[CH:8]2.Cl.O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.CO.C(OCC)(=O)C>[OH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[C:9]([C:16]1[N:17]=[N:18][N:19]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]4[CH:39]=[CH:38][C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[N:31]=4)[CH:23]=3)[N:20]=1)=[CH:8]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 135574110HCID 135574110, compound

Product 1

HCID 135528948HCID 135528948, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21584188Chloroform methanolSolvent

Procedure

6-methoxymethoxy-3-{2-[3-(2-quinolylmethoxy)-benzyl]tetrazolyl}quinolin-2-one (444 mg, 0.85 mmol) was dissolved in a mixture (100 ml) of chloroform-methanol (10:1). A solution (5 ml) of hydrochloric acid (4N) in ethyl acetate was added to the resultant mixture, and the mixture was stirred at room temperature for 17 hours. Water (400 ml) was added thereto, and a saturated aqueous solution of sodium hydrogencarbonate was added dropwise so as to neutralize the aqueous phase, followed by extraction with a mixture of chloroform-methanol (10:1). The organic phase was dried over magnesium sulfate anhydrate, and the solvent was removed under reduced pressure. The residue was recrystallized from a chloroform-methanol-diethylether mixture, to thereby obtain the title compound as yellow leaf crystals (353 mg, 0.74 mmol, 87.2%).

Workup

  1. extractionfollowed by extraction with a mixture of chloroform-methanol (10:1)
  2. dry with materialThe organic phase was dried over magnesium sulfate anhydrate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was recrystallized from a chloroform-methanol-diethylether mixture

Sources & evidence

ORD record
ord-57647da13ee4489f8e4e57a79f74e32a
Source dataset
uspto-grants-2000_09
Patent number
US06121286

Reaction notes

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