Hydrochloric Acid → 4-Cyano-4'-trifluoromethylbutyrophenone O-(2-aminoethyl) oxime hydrochloride

HRID 2083394Notes

Reaction equation

HRID 2083394 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1)=O)#[N:2].[ClH:18].Cl.[NH2:20][O:21][CH2:22][CH2:23][NH2:24].N1C=CC=CC=1.Cl>C(O)C>[ClH:18].[NH2:24][CH2:23][CH2:22][O:21][N:20]=[C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1)[CH2:5][CH2:4][CH2:3][C:1]#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 143623262-(O-aminooxy)ethylamine dihydrochlorideHCID 203585325-Oxo-5-(4-trifluoromethylphenyl)valeronitrile

Product 1

HCID 867356254-Cyano-4'-trifluoromethylbutyrophenone O-(2-aminoethyl) oxime hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

5.6 Mmol (1.35 g) of 4-cyano-4'-trifluoromethylbutyrophenone, 5.6 mmol (0.84 g) of 2 aminooxyethylamine dihydrochloride and 0.8 ml of pyridine were refluxed in 20 ml of absolute ethanol for 2.5 hours. The processing was equal to that of example 1. The resulting free base was dissolved in absolute ethanol and an equivalent quantity of 2N alcoholic hydrochloric acid was added. The ethanol was then removed in vacuo and the residue was crystallized twice from ethanol/ether (1:5). The melting point of the resulting title compound was 136°-136.5° C.

Workup

  1. customThe ethanol was then removed in vacuo
  2. customthe residue was crystallized twice from ethanol/ether (1:5)
  3. customwas 136°-136.5° C.

Sources & evidence

ORD record
ord-cd98fd0404eb4f61809f5482a0c88104
Source dataset
uspto-grants-1978_04
Patent number
US04085225

Reaction notes

Loading…