Sodium Hydroxide → 4-[5-[4-[amino(hydroxyimino)methyl]phenoxy]pentyloxy]-N,N-bis-(1-methylethyl)benzamide

HRID 2209733Notes

Reaction equation

HRID 2209733 reaction equation
[C:1]([C:3]1[CH:30]=[CH:29][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:28]=[CH:27][C:17]([C:18]([N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])=[O:19])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1)#[N:2].[OH-:31].[Na+].Cl.[NH2:34]O>O.C(O)C>[NH2:2][C:1](=[N:34][OH:31])[C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]([N:20]([CH:21]([CH3:22])[CH3:23])[CH:24]([CH3:25])[CH3:26])=[O:19])=[CH:27][CH:28]=2)=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 193814984-[5-(4-cyanophenoxy)pentyloxy]N,N-bis(1-methylethyl)benzamide

Product 1

HCID 536542184-[5-[4-[amino(hydroxyimino)methyl]phenoxy]pentyloxy]-N,N-bis-(1-methylethyl)benzamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A stirred solution of 4-[5-(4-cyanophenoxy)-pentyloxy]-N,N-bis(1-methylethyl)benzamide (300 mg, 0.73 mmol) in 2 mL of water and 8 mL of ethanol is treated with sodium hydroxide (32 mg, 0.81 mmol) and hydroxylamine hydrochloride (56 mg, 0.81 mmol). After refluxing overnight, the reaction is partitioned between dichloromethane and brine. The organic phase is dried over sodium sulfate, and concentrated in vacuo. The resulting material is purified by chromatography on silica gel (10 g) with 70-80% ethyl acetate/hexane as the eluent to afford 4-[5-[4-[amino(hydroxyimino)methyl]phenoxy]pentyloxy]-N,N-bis -(1-methylethyl)benzamide as colorless crystals, m.p.=146°-149° C.;

Workup

  1. temperatureAfter refluxing overnight
  2. customthe reaction is partitioned between dichloromethane and brine
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting material is purified by chromatography on silica gel (10 g) with 70-80% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record
ord-f981e22a24954f09a6132d004079303f
Source dataset
uspto-grants-1995_10
Patent number
US05455274

Reaction notes

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