Hydroxyamine hydrochloride → HCID 9584179, compound

HRID 1941881Notes

Reaction equation

HRID 1941881 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.Cl.[NH2:15][OH:16].C(=O)(O)[O-].[Na+]>CO>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:13]=[CH:12][C:9](/[C:10](=[N:15]/[OH:16])/[NH2:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 27784284-(1,3-Dioxolan-2-yl)benzonitrile

Product 1

HCID 9584179HCID 9584179, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(1,3-dioxolan-2-yl)benzonitrile (16.4 g, 93.6 mmol), hydroxylamine hydrochloride (9.76 g, 140 mmol) and sodium bicarbonate (15.7 g, 187 mmol) in MeOH (100 mL) was heated to reflux for 4 hr. After cooling to RT, the reaction mixture was filtered and the filtrate was concentrated to provide solids that were collected by filtration and washed with cold methanol to provide (Z)-4-(1,3-dioxolan-2-yl)-N′-hydroxybenzimidamide (16 g, 76.8 mmol). The compound had an HPLC retention time=0.38 min. —CHROMOLITH® SpeedROD 4.6×30 mm. flow=5 mL/min (2 min. gradient); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1=209.2

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hr
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customto provide solids that
  6. filtrationwere collected by filtration
  7. washwashed with cold methanol

Sources & evidence

ORD record
ord-e43c7a1e3db14e9895036c05855090b0
Source dataset
uspto-grants-2013_03
Patent number
US08389509B2

Reaction notes

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