Toluene → HCID 178510799, compound

HRID 470638Notes

Reaction equation

HRID 470638 reaction equation
Cl.[NH2:2][OH:3].C(=O)(O)[O-].[Na+].[CH:9]1([CH2:15][C:16]#[N:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C1(C)C=CC=CC=1>C(O)(C)C>[CH:9]1([CH2:15][C:16](=[NH:17])[NH:2][OH:3])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 109534882-cyclohexylacetonitrile

Product 1

HCID 178510799HCID 178510799, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 0.846 g (8.1 mmol) of hydroxylamine hydrochloride in 11 mL of isopropyl alcohol, 1.499 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 (8.1 mmol) of 2-cyclohexylacetonitrile was added and stirred at 80° C. to 85° C. for 3-4 h. After completion of the reaction, 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 was chased with 5 mL of toluene to yield the title compound.

Workup

  1. stirringstirred at 80° C. to 85° C. for 3-4 h
  2. customAfter completion of the reaction
  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-b29c8926bcc2492589d70dcbbdec6512
Source dataset
uspto-grants-2014_01
Patent number
US08629277B2

Reaction notes

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