Sodium Hydroxide → HCID 53720923, compound

HRID 2209736Notes

Reaction equation

HRID 2209736 reaction equation
[C:1]([C:3]1[CH:31]=[CH:30][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:27]=[CH:26][C:16]([C:17]([N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])=[O:18])=[CH:15][C:14]=2[O:28][CH3:29])=[CH:5][CH:4]=1)#[N:2].[OH-:32].[Na+].Cl.[NH2:35]O>O.C(O)C>[NH2:2][C:1](=[N:35][OH:32])[C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:27]=[CH:26][C:16]([C:17]([N:19]([CH:23]([CH3:24])[CH3:25])[CH:20]([CH3:21])[CH3:22])=[O:18])=[CH:15][C:14]=2[O:28][CH3:29])=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 19381508HCID 19381508, compound

Product 1

HCID 53720923HCID 53720923, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A stirred solution of 4-[4-(4-cyanophenoxy)butoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide (500 mg, 1.18 mmol) in 2 mL of water and 8 mL of ethanol is treated with sodium hydroxide (57.7 mg, 1.34 mmol) and hydroxylamine hydrochloride (90 mg, 1.29 mmol). After refluxing overnight, the reaction is partitioned between dichloromethane and brine. The organic phase is dried over magnesium sulfate, and concentrated in vacuo. The resulting material is purified by chromatography on silica gel (15 g) with ethyl acetate as the eluent to afford 4- [4-[4-[amino(hydroxyimino)methyl]phenoxy]butoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide as colorless crystals, mp=63°-65° C.;

Workup

  1. temperatureAfter refluxing overnight
  2. customthe reaction is partitioned between dichloromethane and brine
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting material is purified by chromatography on silica gel (15 g) with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-1e8ef46ba0c841189464530b77dab8a0
Source dataset
uspto-grants-1995_10
Patent number
US05455274

Reaction notes

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