Hydrochloric Acid → HCID 12639347, compound

HRID 1910816Notes

Reaction equation

HRID 1910816 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]#[N:13])=[CH:7][CH:6]=1)([O-:4])=[O:3].[CH2:14]([OH:16])[CH3:15]>>[ClH:1].[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12](=[NH:13])[O:16][CH2:14][CH3:15])=[CH:9][CH:10]=1)([O-:4])=[O:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 68386p-Nitrophenylacetonitrile

Product 1

HCID 12639347HCID 12639347, compoundYield 47%

Procedure

Hydrogen chloride gas was passed through a solution of 4-nitrophenyl acetonitrile (5.0 g, 30.8 mmol) in ethanol (400 mL) until saturation, keeping the temperature between 0-5° C. The solvent was removed under reduced pressure at 15° C. to give a residue which on trituration with diethyl ether gave a solid. The solid was filtered under a nitrogen atmosphere and washed thoroughly with diethyl ether. Drying under vacuum afforded ethyl 2-(4-nitrophenyl)-acetimidate hydrochloride (3.5 g, 47%) which was hygroscopic in nature.

Workup

  1. custombetween 0-5° C
  2. customThe solvent was removed under reduced pressure at 15° C.
  3. customto give a residue which on trituration with diethyl ether
  4. customgave a solid
  5. filtrationThe solid was filtered under a nitrogen atmosphere
  6. washwashed thoroughly with diethyl ether
  7. customDrying under vacuum

Sources & evidence

ORD record
ord-1c2b43cada934eb39f6cde83fcd75ada
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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