Hydroxyamine hydrochloride → HCID 86603024, compound

HRID 735463Notes

Reaction equation

HRID 735463 reaction equation
C1(C(C2C=CC=CC=2)=[N:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[N:16]([CH2:28][C:29]4[C:34]([F:35])=[CH:33][C:32]([F:36])=[CH:31][C:30]=4[F:37])[N:17]=[C:18]4[C:23]=3[CH:22]=[CH:21][CH:20]=[C:19]4[C:24]([F:27])([F:26])[F:25])[CH:10]=2)C=CC=CC=1.C([O-])(=O)C.[Na+].Cl.NO>CO>[F:35][C:34]1[CH:33]=[C:32]([F:36])[CH:31]=[C:30]([F:37])[C:29]=1[CH2:28][N:16]1[C:15]([C:11]2[CH:10]=[C:9]([NH2:8])[CH:14]=[CH:13][CH:12]=2)=[C:23]2[C:18]([C:19]([C:24]([F:25])([F:26])[F:27])=[CH:20][CH:21]=[CH:22]2)=[N:17]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86603025HCID 86603025, compound

Product 1

HCID 86603024HCID 86603024, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Then a solution of N-(diphenylmethylene)-N-{3-[2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-yl]phenyl}amine (0.77 g, 1.31 mmol) in methanol (10 mL) was treated with sodium acetate (0.25 g, 3 mmol) and hydroxylamine hydrochloride (0.15 g, 2.2 mmol), and stirred at room temperature for 2 hours. The methanol was evaporated and the residue slurried in ether, the inorganic solid filtered off, and the ether stripped to afford crude product, which was purified by flash chromatography (silica 60, 10% hexane/ethyl acetate) to afford the title compound (0.28 g, 50%).

Workup

  1. customThe methanol was evaporated
  2. filtrationthe inorganic solid filtered off
  3. customto afford crude product, which
  4. customwas purified by flash chromatography (silica 60, 10% hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9ca8c45ca9b24fe08e24b2bc19e4dcde
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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