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

HRID 1406579Notes

Reaction equation

HRID 1406579 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 room temp 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-5142a06f0f574bde844e58a458dd9dec
Source dataset
uspto-grants-2014_12
Patent number
US08916600B2

Reaction notes

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