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

HRID 1988387Notes

Reaction equation

HRID 1988387 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-8d86eec9d66f4c7da6304f2ab769c0f4
Source dataset
uspto-grants-2009_06
Patent number
US07553972B2

Reaction notes

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