Ethyl Acetate → HCID 178507702, compound

HRID 1793389Notes

Reaction equation

HRID 1793389 reaction equation
O.O.[Sn](Cl)Cl.[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:28](=[O:29])[C:18]3=[CH:19][NH:20][C:21]4[C:22]([F:27])=[CH:23][CH:24]=[CH:25][C:26]=4[C:17]3=[N:16]2)=[CH:11][CH:10]=1)([O-])=O.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:6][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:28](=[O:29])[C:18]3=[CH:19][NH:20][C:21]4[C:22]([F:27])=[CH:23][CH:24]=[CH:25][C:26]=4[C:17]3=[N:16]2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 178515232HCID 178515232, compound2×

Product 1

HCID 178507702HCID 178507702, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Tin (II) chloride dihydrate (12.5 g, 0.055 mol) was added in one portion to a stirred solution of 2-(4-nitro-phenyl)-6-fluoro-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one (intermediate 1) (3.59 g, 0.011 mol) in ethyl alcohol (110 ml) at room temperature. The mixture was then heated to 80° C. for 8 h, cooled to room temperature and filtered to leave a yellow solid. The solid was suspended in a bi-phasic solution of ethyl acetate (1L), a saturated solution of Rochelles salt (500 ml) and a saturated solution of sodium bicarbonate (500 ml) and stirred at room temperature for 2 h. The mixture was filtered and the remaining solid was washed with water and dried under vacuum to afford the title compound (3.39 g, 99%) as a bright yellow solid, LCMS m/z 295.30 [M+H]+ @ RT 0.84 min.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customto leave a yellow solid
  4. filtrationThe mixture was filtered
  5. washthe remaining solid was washed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-7712dc9388da484a8a072bcd7f76f278
Source dataset
uspto-grants-2006_07
Patent number
US07081456B2

Reaction notes

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