Water → HCID 58134788, compound

HRID 444760Notes

Reaction equation

HRID 444760 reaction equation
[F:1][C:2]1[C:3]([N+:24]([O-])=O)=[C:4]2[C:9]3=[C:10]([O:13][CH2:14][C:15]4([CH2:19][CH2:18][CH2:17][CH2:16]4)[N:8]3[CH:7]=[C:6]([C:20]([NH2:22])=[O:21])[C:5]2=[O:23])[C:11]=1[F:12].S(S([O-])=O)([O-])=O.[Na+].[Na+].O>O.CO>[NH2:24][C:3]1[C:2]([F:1])=[C:11]([F:12])[C:10]2[O:13][CH2:14][C:15]3([CH2:16][CH2:17][CH2:18][CH2:19]3)[N:8]3[C:9]=2[C:4]=1[C:5](=[O:23])[C:6]([C:20]([NH2:22])=[O:21])=[CH:7]3

Participants

5

Reactant 3

HCID 962WaterHCID 24489Sodium DithioniteHCID 58134856HCID 58134856, compound

Product 1

HCID 58134788HCID 58134788, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a suspension of 9,10-difluoro-8-nitro-7-oxo-2,7-dihydrospiro[[1,4]oxazino[2,3,4-ij]quinoline-3,1′-cyclopentane]-6-carboxamide (1 g, 2.7 mmol) in a mixture of water/methanol (1:1 v/v, 30 mL) was added sodium hydrosulfite (Na2S2O4, 3.75 g, 22 mmol). The suspension was refluxed for 5 h until all starting material had disappeared. Upon completion, the reaction mixture was cooled to room temperature and 50 ml of water were added. After 20 minutes, a light yellow solid was collected by filtration and washed with water. The solid was dried under vacuo to give 660 mg (73% yield) of the title compound that was used without further purification in the next step.

Workup

  1. temperatureThe suspension was refluxed for 5 h until all starting material
  2. filtrationa light yellow solid was collected by filtration
  3. washwashed with water
  4. customThe solid was dried under vacuo

Sources & evidence

ORD record
ord-27e83d3faefd406683863e335e0eebe7
Source dataset
uspto-grants-2013_07
Patent number
US08476261B2

Reaction notes

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