Toluene → N'-hydroxynonanimidamide

HRID 470641

Reaction equation

HRID 470641 reaction equation
Cl.[NH2:2][OH:3].C(=O)(O)[O-].[Na+].[C:9](#[N:18])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C1(C)C=CC=CC=1>C(O)(C)C>[OH:3][NH:2][C:9](=[NH:18])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 1140TolueneHCID 16715NonanenitrileHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 5074022N'-hydroxynonanimidamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 0.74 g (10.7 mmol) of hydroxylamine hydrochloride in 11 mL of isopropyl alcohol, 1.327 g (17.8 mmol) of sodium bicarbonate was added. The resulting mixture was stirred at 25° C. to 30° C. for 10-15 min. 1.0 g (7.1 mmol) of nonanenitrile was added and stirred at 80° C. to 85° C. for 3-4 h. After the reaction period, the reaction mixture was cooled to 25° C. to 30° C., filtered and washed with 2 mL of isopropyl alcohol. The filtrate was collected and distilled out completely to obtain a crude residue. The residue with chased with 5 mL of toluene below 45° C., under vacuum, to yield the title compound.

Workup

  1. stirringstirred at 80° C. to 85° C. for 3-4 h
  2. customAfter the reaction period
  3. temperaturethe reaction mixture was cooled to 25° C. to 30° C.
  4. filtrationfiltered
  5. washwashed with 2 mL of isopropyl alcohol
  6. customThe filtrate was collected
  7. distillationdistilled out completely
  8. customto obtain a crude residue

Sources & evidence

ORD record
ord-d41592d5c71f4ecb8defc356914eac8c
Source dataset
uspto-grants-2014_01
Patent number
US08629277B2

Linked notes

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