Hydroxyamine hydrochloride → HCID 58432028, compound

HRID 1798650Notes

Reaction equation

HRID 1798650 reaction equation
[CH2:1]([O:3][CH:4]([O:6][CH:7]([CH:10]([O:23][CH3:24])[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1)[C:8]#[N:9])[CH3:5])[CH3:2].[NH2:25][OH:26].Cl.C([O-])(O)=O.[Na+]>CO>[CH2:1]([O:3][CH:4]([O:6][CH:7]([CH:10]([O:23][CH3:24])[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)=[CH:13][CH:12]=1)/[C:8](=[N:25]/[OH:26])/[NH2:9])[CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 58432122HCID 58432122, compound

Product 1

HCID 58432028HCID 58432028, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 2-(1-ethoxyethoxy)-3-methoxy-3-(4-morpholinophenyl)propanenitrile (0.60 g, 1.8 mmol) in anhydr MeOH (10 mL) under argon was added NH2OH.HCl (0.175 g, 2.5 mmol) and NaHCO3 (0.234 g, 2.8 mmol). The reaction was heated briefly at 75° C. then at 60° C. for 16 hrs. After cooling to room temp, the mixture was concentrated in vacuo to give (Z)-2-(1-ethoxyethoxy)-N′-hydroxy-3-methoxy-3-(4-morpholinophenyl)propanimidamide which was used in the next synthetic step without further purification (0.777 g).

Workup

  1. temperatureAfter cooling to room temp
  2. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-786413b1f3a0492a8333c83ad07bc720
Source dataset
uspto-grants-2013_01
Patent number
US08343970B2

Reaction notes

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