Ethanone, 2-(4-chlorophenyl)-1-phenyl- → HCID 85675368, compound

HRID 850293Notes

Reaction equation

HRID 850293 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=[CH:4][CH:3]=1.Cl.[O:18]([NH2:20])[CH3:19]>N1C=CC=CC=1>[CH3:19][O:18][N:20]=[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 95829Ethanone, 2-(4-chlorophenyl)-1-phenyl-HCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 85675368HCID 85675368, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-(4-chlorophenyl)-1-phenyl-1-ethanone (2, 1.93 g, 8.37 mmol) in 25 ml pyridine (dried over molecular sieves) under nitrogen was added at room temperature methoxylamine hydrochloride (873 mg, 10.5 mmol). The resulting slightly cloudy, pale orange mixture was stirred at room temperature overnight. The pyridine was removed in vacuo with heating. The residual solids were stirred with ether (60 ml), isolated by filtration, and discarded. The filtrate was dried over sodium sulfate, and concentrated in vacuo to give a mixture of the oxime geometrical isomers as 2.00 g of a clear, pale yellow syrup (92% yield). 1H NMR showed the isomers to be formed in a 5:3 ratio: Rf 0.64, 0.50; IR (CDCl3) 3068 (w), 2940 (m), 2819 (w), 1602 (w), 1493 (s), 1442 (m); 1H NMR (CDCl3) 7.63 (m, 2H), 7.37-7.11 (m, 11.5 H), 4.12 (s, 2H), 4.05 (s, 3H), 3.91 (s, 1.6H), 3.82 (s, 1.2H); low resolution mass spec. 259 (M+, 8), 227 (100), 192 (28), 165 (18), 134 (12), 125 (62), 119 (37).

Workup

  1. customThe pyridine was removed in vacuo
  2. temperaturewith heating
  3. stirringThe residual solids were stirred with ether (60 ml)
  4. customisolated by filtration
  5. dry with materialThe filtrate was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give

Sources & evidence

ORD record
ord-92098f08b7534645a60231142a86b7a4
Source dataset
uspto-grants-2000_01
Patent number
US06017910

Reaction notes

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