Citric Acid → HCID 178464894, compound

HRID 2246625Notes

Reaction equation

HRID 2246625 reaction equation
[I:1]I.[CH2:3]([NH:5][C:6](=[O:24])[C:7]1[CH:12]=[C:11]([C:13]2[CH:21]=[C:20]3[C:16]([CH:17]=[N:18][NH:19]3)=[CH:15][CH:14]=2)[C:10]([CH3:22])=[C:9]([F:23])[CH:8]=1)[CH3:4].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1.[OH-].[Na+].O>[CH2:3]([NH:5][C:6](=[O:24])[C:7]1[CH:12]=[C:11]([C:13]2[CH:21]=[C:20]3[C:16]([C:17]([I:1])=[N:18][NH:19]3)=[CH:15][CH:14]=2)[C:10]([CH3:22])=[C:9]([F:23])[CH:8]=1)[CH3:4]

Participants

8

Reactant 4

HCID 311Citric AcidHCID 807IodineHCID 656671Sodium PyrosulfiteHCID 60133232N-ethyl-3-fluoro-5-(1H-indazol-6-yl)-4-methylbenzamide2×

Product 1

HCID 178464894HCID 178464894, compoundYield 98.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

Iodine (0.153 g) was added to a stirred solution of N-ethyl-3-fluoro-5-(1H-indazol-6-yl)-4-methylbenzamide (Intermediate 18, 0.15 g) in 1,4-dioxan (4 ml) and aqueous sodium hydroxide (2M, 4 ml) then stirred at room temperature for 45 min. The reaction mixture was treated aqueous citric acid (20%, 20 ml) followed by sodium metabisulphite (2 g). The mixture was diluted with water then extracted with ethyl acetate (2×30 ml). The organic extracts were washed with water (30 ml) dried (Na2SO4) and concentrated under vacuum to give the title-compound as a pale yellow foam (0.21 g).

Workup

  1. extractionthen extracted with ethyl acetate (2×30 ml)
  2. washThe organic extracts were washed with water (30 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-56e6afe5697f482299adb484f834215c
Source dataset
uspto-grants-2010_03
Patent number
US07687532B2

Reaction notes

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