Sodium Hydroxide → 4-[5-[4-[amino(hydroxyimino)methyl]-3-fluoro-phenoxy]pentyloxy]-N,N-bis (1-methylethyl)benzamide

HRID 2209739Notes

Reaction equation

HRID 2209739 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][C:4]=1[F:31])#[N:2].[OH-:32].[Na+].Cl.[NH2:35]O>C(O)C>[NH2:2][C:1](=[N:35][OH:32])[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:15]=[CH:16][C:17]([C:18]([N:20]([CH:24]([CH3:25])[CH3:26])[CH:21]([CH3:23])[CH3:22])=[O:19])=[CH:27][CH:28]=2)=[CH:5][C:4]=1[F:31]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 193814994-[5-(4-cyano-3-fluoro-phenoxy)pentyloxy]-N,N-bis(1-methylethyl)benzamide

Product 1

HCID 543034514-[5-[4-[amino(hydroxyimino)methyl]-3-fluoro-phenoxy]pentyloxy]-N,N-bis (1-methylethyl)benzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 4-[5-(4-cyano-3-fluoro-phenoxy)pentyloxy]-N,N-bis(1-methylethyl)benzamide (360 mg, 0.84 mmol) in 1.7 mL of 1N sodium hydroxide (1.7 mmol) and 10 mL of ethanol is treated with hydroxylamine hydrochloride (120 mg, 1.7 mmol). After refluxing overnight, the reaction is concentrated in vacuo. The resulting material is purified by chromatography on silica gel (500 g) with 60-70% ethyl acetate/hexane as the eluent to afford 4-[5-[4-[amino(hydroxyimino)methyl]-3-fluoro-phenoxy]pentyloxy]-N,N-bis (1-methylethyl)benzamide as a colorless foam;

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 60-70% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record
ord-3ed75856c8124fa28a37bbcbaf7465c7
Source dataset
uspto-grants-1995_10
Patent number
US05455274

Reaction notes

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