Hydrazine hydrate (1:1) → HCID 178509230, compound

HRID 1909161Notes

Reaction equation

HRID 1909161 reaction equation
Cl[C:2]1[N:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[C:4]#[N:5].O.[NH2:12][NH2:13]>C(O)CCC>[F:10][C:7]1[CH:6]=[C:3]2[C:4]([NH2:5])=[N:13][NH:12][C:2]2=[N:9][CH:8]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 231108512-Chloro-5-fluoropyridine-3-carbonitrile

Product 1

HCID 178509230HCID 178509230, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of compound 4 (50 g, 321.7 mmol) in 1-butanol (1 L) was added hydrazine monohydrate (150 mL, 3.2 mol), and the mixture was refluxed for 4 h. The mixture was cooled to room temperature and concentrated. The precipitate was successively washed on filter with water (2×) and Et2O (2×) and dried in vacuo overnight to give compound 5 (44 g, 88%) as a yellow solid. 1H NMR (DMSO-d6, 300 MHz): δ 5.53 (s, 2H); 7.94 (dd, 1H); 8.35 (dd, 1H); 12.02 (s, 1H).

Workup

  1. temperaturethe mixture was refluxed for 4 h
  2. concentrationconcentrated
  3. washThe precipitate was successively washed
  4. filtrationon filter with water (2×) and Et2O (2×)
  5. customdried in vacuo overnight

Sources & evidence

ORD record
ord-70e609d3d4194348900347801978fcf9
Source dataset
uspto-grants-2013_12
Patent number
US08598361B2

Reaction notes

Loading…