Hydroxyamine hydrochloride → 6-(2-Dimethylamino-1,1-dimethyl-ethoxy)-pyridazin-3-ylamine

HRID 449644Notes

Reaction equation

HRID 449644 reaction equation
[CH3:1][N:2]([CH3:28])[CH2:3][C:4]([CH3:27])([O:6][C:7]1[N:12]=[N:11][C:10]([N:13]=C(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:9][CH:8]=1)[CH3:5].Cl.NO.C([O-])(=O)C.[Na+]>CO>[CH3:1][N:2]([CH3:28])[CH2:3][C:4]([CH3:5])([CH3:27])[O:6][C:7]1[N:12]=[N:11][C:10]([NH2:13])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866623216-(1-(dimethylamino)-2-methylpropan-2-yloxy)-N-(diphenylmethylene)pyridazin-3-amine

Product 1

HCID 667429246-(2-Dimethylamino-1,1-dimethyl-ethoxy)-pyridazin-3-ylamineYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 10 mL pear shape flask was added 6-(1-(dimethylamino)-2-methylpropan-2-yloxy)-N-(diphenylmethylene)pyridazin-3-amine (200 mg, 534 μmol, Eq: 1.00) and MeOH (5.34 ml). To the mixture was added hydroxylamine hydrochloride (66.8 mg, 961 μmol, Eq: 1.8) and sodium acetate (105 mg, 1.28 mmol, Eq: 2.4). The mixture was stirred at room temperature for 25 min. The reaction mixture was absorbed on to silica and purified by LC chromatography eluting with 0-5% (10% NH4OH in MeOH) in 1/1 EtOAc/Hexane to afford 110 mg (98%) of the title compound.

Workup

  1. customThe reaction mixture was absorbed on to silica
  2. custompurified by LC chromatography
  3. washeluting with 0-5% (10% NH4OH in MeOH) in 1/1 EtOAc/Hexane

Sources & evidence

ORD record
ord-7e80b72d6289410593a061fad781acd1
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

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