Benzoyl chloride → HCID 23373333, compound

HRID 2244152Notes

Reaction equation

HRID 2244152 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][C:9]2[CH:14]=[CH:13][N+:12]([O-])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C[Si]([C:22]#[N:23])(C)C.C(Cl)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.O>[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:22]#[N:23])[CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 82115Trimethylsilyl cyanideHCID 2755771HCID 2755771, compound

Product 1

HCID 23373333HCID 23373333, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-nitro-benzyl)-pyridine I-oxide (1.0 g, 4.3 mmol) in dichloromethane (9 mL) was added trimethylsilyl cyanide (2.3 mL, 17 mmol). After 5 min, benzoyl chloride (1.0 mL, 8.7 mmol) was added dropwise and the mixture was stirred at rt for an additional 30 min. Water (10 mL) was carefully added, followed by solid potassium carbonate (2.1 g). After 30 min, the aqueous phase was extracted with dichloromethane and the combined organic layers were dried over sodium sulfate and concentrated in vacuo. Purification of the residue by column chromatography, eluting with 5-25% ethyl acetate in hexanes, gave an orange oil. This oil was subsequently triturated with toluene to afford 4-(4-nitro-benzyl)-pyridine-2-carbonitrile as a tan solid (353 mg, 34%). 1H NMR (CHCl3-d) δ 8.63 (d, J=4.8 Hz, 1H), 8.21 (m, 2H), 7.49 (m, 1H), 7.32 (m, 3H), 4.15 (s, 2H).

Workup

  1. waitAfter 30 min
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by column chromatography
  6. washeluting with 5-25% ethyl acetate in hexanes
  7. customgave an orange oil
  8. customThis oil was subsequently triturated with toluene

Sources & evidence

ORD record
ord-af4d26f2ac324fb88c5f0dcd0fc2975a
Source dataset
uspto-grants-2010_03
Patent number
US07678804B2

Reaction notes

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