Hydroxyamine hydrochloride → 2-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(hydroxyimino-methyl)-benzamide

HRID 456889Notes

Reaction equation

HRID 456889 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:5].Cl.[NH2:23][OH:24].C([O-])(=O)C.[Na+]>CO.O>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([CH:20]=[N:23][OH:24])=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:5]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 865959112-chloro-5-formyl-N-(1-hydroxy-cycloheptylmethyl)-benzamide

Product 1

HCID 724346312-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(hydroxyimino-methyl)-benzamideYield 45.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 2-chloro-5-formyl-N-(1-hydroxy-cycloheptylmethyl)-benzamide (290 mg, 0.94 mmol), hydroxylamine hydrochloride (78 mg, 1.13 mmol) and sodium acetate (223 mg, 2.72 mmol) in methanol (5 mL) and water (5 mL) was stirred at room temperature for 3 h. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water, and brine, dried over sodium sulfate, filtered and adsorbed onto silica gel. The residue was purified by chromatography (1:1 ethyl acetate-hexane) to afford the title compound (140 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with water, and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customThe residue was purified by chromatography (1:1 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-6ae7d8d138c6474f9c667e9ca739d301
Source dataset
uspto-grants-2007_03
Patent number
US07186742B2

Reaction notes

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