Hydrazine hydrate (1:1) → 6-{[({(3-Bromo-4-methoxyphenyl)[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methylene}amino)oxy]methyl}pyridin-2-amine

HRID 875200Notes

Reaction equation

HRID 875200 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10](=[N:22][O:23][CH2:24][C:25]2[N:30]=[C:29]([N:31]3C(=O)C4C(=CC=CC=4)C3=O)[CH:28]=[CH:27][CH:26]=2)[C:11]2[C:16]([Cl:17])=[CH:15][C:14]([C:18]([F:21])([F:20])[F:19])=[CH:13][N:12]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].O.NN>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:10](=[N:22][O:23][CH2:24][C:25]2[N:30]=[C:29]([NH2:31])[CH:28]=[CH:27][CH:26]=2)[C:11]2[C:16]([Cl:17])=[CH:15][C:14]([C:18]([F:20])([F:21])[F:19])=[CH:13][N:12]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866507382-(6-{[({(3-bromo-4-methoxyphenyl)[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methylene}amino)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 866507396-{[({(3-Bromo-4-methoxyphenyl)[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methylene}amino)oxy]methyl}pyridin-2-amineYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(6-{[({(3-bromo-4-methoxyphenyl)[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methylene}amino)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione (7.00 g, 9.75 mmol) in tetrahydrofuran (150 mL) was added hydrazine hydrate (2.37 mL, 48.7 mmol) dropwise. After stirring overnight at room temperature, the reaction mixture was filtered, and the filtrate concentrated in vacuo. Purification on silica gel afforded 6-{[({(3-bromo-4-methoxyphenyl)[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methylene}amino)oxy]methyl}pyridin-2-amine as an oil [4.00 g, yield 75%; HPLC/MS: m/z=516 (M+H); log P(HCOOH)=2.54].

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customPurification on silica gel

Sources & evidence

ORD record
ord-cdc46676546946a5afb8e8bf7144e3cc
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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