Hydrochloric Acid → 3-(2-(2-Fluoro-5-iodobenzylidene)hydrazinyl)benzoic acid

HRID 1098943Notes

Reaction equation

HRID 1098943 reaction equation
[NH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])[NH2:2].[F:12][C:13]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:14]=1[CH:15]=O.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C.O>[F:12][C:13]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:14]=1[CH:15]=[N:2][NH:1][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 27365213-Hydrazinobenzoic acidHCID 162170582-Fluoro-5-iodobenzaldehyde

Product 1

HCID 670412113-(2-(2-Fluoro-5-iodobenzylidene)hydrazinyl)benzoic acidYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-hydrazinylbenzoic acid (1.52 g, 10 mmol)), 2-fluoro-5-iodobenzaldehyde (2.5 g, 10 mmol) and caesium carbonate (3.26 g, 10 mmol) were stirred in DMF (10 mL) at r.t. under argon atmosphere for 2.5 h. Water (40 mL) was added and the clear solution was acidified with aqueous HCl (1.7 M). The beige-orange precipitate that formed was collected by, filtration, washed with water and dried in vacuo to give the title compound (3.75 g, 98%).

Workup

  1. customThe beige-orange precipitate that formed
  2. customwas collected by,
  3. filtrationfiltration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a108aa13808348678cedb1acbe9480d5
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Reaction notes

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