Water → 3-Amino-6-bromo-5-(trifluoromethyl)picolinohydrazide

HRID 574242Notes

Reaction equation

HRID 574242 reaction equation
C[O:2][C:3]([C:5]1[C:10]([NH2:11])=[CH:9][C:8]([C:12]([F:15])([F:14])[F:13])=[C:7]([Br:16])[N:6]=1)=O.O.[NH2:18][NH2:19].O>CO>[NH2:11][C:10]1[C:5]([C:3]([NH:18][NH2:19])=[O:2])=[N:6][C:7]([Br:16])=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 58964428Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate2×

Product 1

HCID 867295953-Amino-6-bromo-5-(trifluoromethyl)picolinohydrazide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of 3-amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (Intermediate A4) (1.00 g, 3.34 mmol) in dry MeOH (20 ml) was stirred at reflux (85° C.) for 30 min and then treated with hydrazine monohydrate (324 ul, 6.69 mmol). The mixture was returned to heat at reflux for 5 h 30 min and allowed to cool to RT. Water was added and the resulting precipitate was collected by filtration and dried in a vacuum oven to afford the title compound as a biege solid;

Workup

  1. temperatureto heat
  2. temperatureat reflux for 5 h 30 min
  3. temperatureto cool to RT
  4. filtrationthe resulting precipitate was collected by filtration
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-2ca61ae5096446678a67f65102e45f12
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

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