Hydrazine hydrate (1:1) → HCID 59320406, compound

HRID 655241Notes

Reaction equation

HRID 655241 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([NH:14][CH3:15])=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:4][CH:3]=1.O.[NH2:20][NH2:21]>N1C=CC=CC=1>[F:18][C:10]1[CH:9]=[C:8]([C:5]2[N:6]=[N:7][C:2]([NH:20][NH2:21])=[CH:3][CH:4]=2)[CH:17]=[CH:16][C:11]=1[C:12]([NH:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86641542HCID 86641542, compound

Product 1

HCID 59320406HCID 59320406, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 4-(6-chloro-pyridazin-3-yl)-2-fluoro-N-methyl-benzamide 34 g (128 mmol) in 500 mL of dry pyridine was cooled in an ice bath and 43.5 mL of hydrazine hydrate was added. The cooling was continued so as to keep the temperature below 30° C. at which time yellow needle separated. The mixture was then heated to 65° C. and stirred overnight. The mixture was filtered and the solid washed with water and Methanol to return the title compound (28.8 g, 84% yield) as a light yellow solid. 1H NMR (300 MHz, DMSO-d6): δ (ppm): 8.27 (s, 2H), 7.96˜7.99 (d, 1H), 7.86˜7.92 (m, 2H), 7.69˜7.75 (m, 1H), 7.09˜7.12 (d, 1H), 4.42 (s, 2H), 2.78˜2.80 (d, 3H); MS (m/z): 262.1 [M++1].

Workup

  1. customthe temperature below 30° C.
  2. customseparated
  3. filtrationThe mixture was filtered
  4. washthe solid washed with water and Methanol

Sources & evidence

ORD record
ord-eee79e42ad5144909b99f49e71402590
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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