Benzoyl chloride → HCID 23373333, compound

HRID 729948Notes

Reaction equation

HRID 729948 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-cda9958865f2469a9e13b405cbd7bb82
Source dataset
uspto-grants-2009_09
Patent number
US07582646B2

Reaction notes

Loading…