Hydrazine hydrate (1:1) → HCID 68975343, compound

HRID 1890944Notes

Reaction equation

HRID 1890944 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:6][N:7]=1.O.[NH2:16][NH2:17]>N1C=CC=CC=1>[F:14][C:10]1[CH:9]=[C:8]([C:5]2[N:4]=[N:3][C:2]([NH:16][NH2:17])=[N:7][CH:6]=2)[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86635018HCID 86635018, compound

Product 1

HCID 68975343HCID 68975343, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 3-chloro-6-(3-fluoro-phenyl)-[1,2,4]triazine (2.09 g, 10.0 mmol) in 13.6 ml of dry pyridine was cooled to 0° C. with ice bath and 1.7 ml of hydrazine hydrate was added. The mixture was then heated to 65° C. and maintained this temperature for ca. 0.5 hour. After cooling down to room temperature, the mixture was poured into ice-water. The resulting solid was recovered by filtration and washed well with water, dried and scratched with hexane to give title compound (1.85 g, 90.2%) as a yellow crystalline solid: 1H NMR (DMSO-d6): δ 8.97 (b, 1H), 8.90 (s, 1H), 7.89-7.82 (m, 2H), 7.59-7.51 (m, 1H), 7.30-˜7.24 (m, 1H), 5.47 (b, 2H); MS (m/z) 206 [M+H+]+.

Workup

  1. temperaturemaintained this temperature for ca. 0.5 hour
  2. temperatureAfter cooling down to room temperature
  3. filtrationThe resulting solid was recovered by filtration
  4. washwashed well with water
  5. customdried

Sources & evidence

ORD record
ord-23e45a52ca0f4c7eaa852e9383ae1f2c
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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