2,6-Difluorophenylhydrazine → HCID 66668374, compound

HRID 1186815Notes

Reaction equation

HRID 1186815 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][NH2:10].F[C:12]1[N:19]=[CH:18][CH:17]=[C:16]([I:20])[C:13]=1[CH:14]=O>CN1C(=O)CCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:12]2=[N:19][CH:18]=[CH:17][C:16]([I:20])=[C:13]2[CH:14]=[N:10]1

Participants

4

Reactant 2

HCID 27789212,6-DifluorophenylhydrazineHCID 99923282-Fluoro-4-iodopyridine-3-carbaldehyde

Product 1

HCID 66668374HCID 66668374, compoundYield 111.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
185 °C

Procedure

To a dry 15 mL ChemGlass pressure bottle under N2 was added (2,6-difluorophenyl)hydrazine (431 mg, 2.99 mmol), 2-fluoro-4-iodonicotinaldehyde (750 mg, 2.99 mmol) and anhydrous NMP (4.5 mL). The reaction mixture was flushed with argon, securely capped and heated to 185° C. for 1.5 h. The reaction mixture was worked up according to the general procedure described in Intermediate 69A to give 1.19 g (quantitative yield) of the title compound (contains approximately 50% of the hydrazone intermediate) as thick, dark oil. LC/MS (Condition B): ret. T=3.5 min, (M+H)+ 357.91.

Workup

  1. customThe reaction mixture was flushed with argon
  2. customsecurely capped

Sources & evidence

ORD record
ord-42f5af261a154c18b337cdf0d9e6437f
Source dataset
uspto-grants-2014_03
Patent number
US08673922B2

Reaction notes

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