Pyridine → HCID 66746431, compound

HRID 471780Notes

Reaction equation

HRID 471780 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[C:12]=1[C:13]#[N:14].N1C=CC=CC=1.[C:28](Cl)(=[O:30])[CH3:29]>C(Cl)Cl>[C:28]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[C:12]=1[C:13]#[N:14])(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 66745963HCID 66745963, compound

Product 1

HCID 66746431HCID 66746431, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(8-hydroxyoctyloxy)-6-nitrobenzonitrile (804 μmol, 235 mg) (Example 274c) was dissolved in dry DCM (10 mL), cooled to 0° C., and treated successively with pyridine (3.216 mmol, 260 μL) and acetyl chloride (1.608 mmol, 114 μL). The reaction mixture was stirred and allowed to warm slowly to room temperature. When the reaction was complete, the volatiles were removed in vacuo and the crude product purified on silica gel (10% to 50% EtOAc in hexanes) to give the desired product (268 mg, 100%). MS 335 (MH+).

Workup

  1. temperatureto warm slowly to room temperature
  2. customthe volatiles were removed in vacuo
  3. customthe crude product purified on silica gel (10% to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5005e73cf38e41a6adade2385da4fbbf
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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