Hydroxyamine hydrochloride → CID 59604233

HRID 1948552Notes

Reaction equation

HRID 1948552 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1.C(=O)(O)[O-].[Na+].Cl.[NH2:18][OH:19]>CC(O)C.C(OCC)(=O)C>[OH:19]/[N:18]=[C:8](\[NH2:9])/[C:7]1[CH:6]=[CH:5][C:4]([CH2:3][CH2:2][OH:1])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 28008154-(2-Hydroxyethyl)benzonitrile

Product 1

HCID 59604233CID 59604233Yield 49%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-(2-hydroxyethyl)benzonitrile (500mg, 3.40 mmol) and sodium bicarbonate (1427 mg, 16.99 mmol) in 2-propanol (50 mL) was added hydroxylamine hydrochloride (472 mg, 6.79 mmol). The reaction mixture was heated at 80° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried MgSO4, filtered, and concentrated to yield 300 mg of (Z)—N′-hydroxy-4-(2-hydroxyethyl)benzimidamide. MS (m+1)=181. HPLC Peak RT=0.13 minutes. (Analytical Method B).

Workup

  1. washwashed with water
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-772c0421d3d64445b75e81c44ff513ad
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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