Sodium Hydroxide → HCID 53685893, compound

HRID 2209723Notes

Reaction equation

HRID 2209723 reaction equation
C([O:4][C:5]1[CH:19]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=2)[CH:17]=[CH:16][C:6]=1[C:7]([N:9]([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11])=[O:8])(=O)C.[OH-:35].[Na+].Cl.[NH2:38]O>O.C(O)C>[NH2:38][C:33](=[N:34][OH:35])[C:30]1[CH:31]=[CH:32][C:27]([O:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][O:20][C:18]2[CH:17]=[CH:16][C:6]([C:7]([N:9]([CH:10]([CH3:11])[CH3:12])[CH:13]([CH3:15])[CH3:14])=[O:8])=[C:5]([OH:4])[CH:19]=2)=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 15295289HCID 15295289, compound

Product 1

HCID 53685893HCID 53685893, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A stirred solution of 2-acetoxy-4-[5-(4-cyanophenoxy)pentyloxy]-N,N-bis(1-methylethyl)benzamide (20 g, 42.9 mmol) in 20 mL of water and 350 mL of ethanol is treated with sodium hydroxide (3.43 g, 85.8 mmol) and hydroxylamine hydrochloride (5.97 g, 85.9 mmol). After refluxing overnight, the reaction is concentrated in vacuo. The resulting material is purified by chromatography on silica gel (500 g) with 65-100% ethyl acetate/hexane followed by 30% methanol/ethyl acetate as the eluent. After concentration in vacuo, the residue is recrystallized with methanol, ethyl acetate, and hexane to afford 4-[5-[4-[amino(hydroxyimino)methyl]phenoxy]pentyloxy]-2-hydroxy-N,N-bis(1-methylethyl)benzamide as colorless crystals, mp=195°-197° C.;

Workup

  1. temperatureAfter refluxing overnight
  2. concentrationthe reaction is concentrated in vacuo
  3. customThe resulting material is purified by chromatography on silica gel (500 g) with 65-100% ethyl acetate/hexane
  4. concentrationAfter concentration in vacuo
  5. customthe residue is recrystallized with methanol, ethyl acetate, and hexane

Sources & evidence

ORD record
ord-d3774d6c04d24820b75531fe270acc4b
Source dataset
uspto-grants-1995_10
Patent number
US05455274

Reaction notes

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