Pyridine → 4-(2-Fluoro-4-iodo-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid hydrazide

HRID 917782Notes

Reaction equation

HRID 917782 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([C:18]([OH:20])=O)=[CH:12][N:13]([CH3:17])[C:14](=[O:16])[CH:15]=1.N1C=CC=CC=1.FC(F)(F)C(OC1C(F)=C(F)C(F)=C(F)C=1F)=O.O.[NH2:46][NH2:47]>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([C:18]([NH:46][NH2:47])=[O:20])=[CH:12][N:13]([CH3:17])[C:14](=[O:16])[CH:15]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24654Hydrazine hydrate (1:1)HCID 4327891Pentafluorophenyl TrifluoroacetateHCID 112346084-(2-Fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid

Product 1

HCID 112350284-(2-Fluoro-4-iodo-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid hydrazide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-(2-fluoro-4-iodo-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (5.62 g, 14.5 mmol) in DMF (50 mL) was added pyridine (3.5 mL, 43.4 mmol) then followed by dropwise addition of pentafluorophenyl trifluoroacetate (4.5 mL, 43.4 mmol). The mixture was stirred at room temperature for 24 hours. To this mixture was added hydrazine monohydrate (2.8 mL, 58 mmol). The reaction mixture was stirred at room temperature for another 24 hours. The precipitated white solid was collected by filtration and washed with water (5 mL) and hexanes. After drying, the 4-(2-Fluoro-4-iodo-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid hydrazide was obtained as a white solid (6.55 g, 81%). 1H NMR [(CD3)2SO, 400 MHz] δ 9.90 (s, 1H), 9.63 (s, 1H), 8.15 (s, 1H), 7.73 (d, 1H), 7.58 (d, 1H), 7.26 (t, 1H), 5.58 (s, 1H), 4.42 (br s, 1H), 2.50 (t, 3H). Anal. Calcd for C15H14FIN2O3: C, 43.3; H, 3.4; N, 6.7. Found: C, 43.7; H, 3.1; N, 7.0.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for another 24 hours
  2. filtrationThe precipitated white solid was collected by filtration
  3. washwashed with water (5 mL) and hexanes
  4. customAfter drying

Sources & evidence

ORD record
ord-ce3bc51173b3441bb88e68f7e6bf3073
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

Loading…