Hydrochloric Acid → 4-Ethyl-2-hydroxy-5-nitrohexanamide

HRID 35576Notes

Reaction equation

HRID 35576 reaction equation
Cl.S(=O)(=O)(O)[OH:3].[CH2:7]([CH:9]([CH:15]([N+:17]([O-:19])=[O:18])[CH3:16])[CH2:10][CH:11]([OH:14])[C:12]#[N:13])[CH3:8]>CCOCC.O>[CH2:7]([CH:9]([CH:15]([N+:17]([O-:19])=[O:18])[CH3:16])[CH2:10][CH:11]([OH:14])[C:12]([NH2:13])=[O:3])[CH3:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 143297994-Ethyl-2-hydroxy-5-nitrohexanenitrile

Product 1

HCID 198516704-Ethyl-2-hydroxy-5-nitrohexanamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of conc. hydrochloric acid (2.4 ml) and conc. sulfuric acid (0.38 ml) was added to a solution of 4-ethyl-2-hydroxy-5-nitrohexanenitrile (1 g) in ether (2 ml) at 0° C. with stirring. The resulting mixture was allowed to stand at room temperature overnight, diluted with cold water, and then extracted with ethyl acetate. The extract was washed with successively with water and 5% aqueous sodium bicarbonate, dried over magnesium sulfate and then evaporated to dryness in vacuo to give 4-ethyl-2-hydroxy-5-nitrohexanamide (0.46 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with successively with water and 5% aqueous sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-ac5cb49d29644e37ae4dbd1f59768f7b
Source dataset
uspto-grants-1988_08
Patent number
US04767768

Reaction notes

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