4-Pyridinemethanamine → 4-Nitrophenyl pyridin-4-ylmethylcarbamate

HRID 1483972Notes

Reaction equation

HRID 1483972 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH2:8])=[CH:3][CH:2]=1.Cl[C:10]([O:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:11]>ClCCl>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:8][C:10](=[O:11])[O:12][C:13]2[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 773174-PyridinemethanamineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 867143034-Nitrophenyl pyridin-4-ylmethylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of pyridin-4-ylmethanamine (505 uL, 5 mmol) and p-nitrophenyl chloroformate (1.0 g, 5 mmol) in dichloromethane (20 mL) was stirred at room temperature for 5 h. Upon completion, the product was collected by vacuum filtration, washed with dichloromethane and purified by preparative HPLC (10-90% acetonitrile in water) to provide 4-nitrophenyl pyridin-4-ylmethylcarbamate as a white solid. MS=274 (MH+).

Workup

  1. filtrationUpon completion, the product was collected by vacuum filtration
  2. washwashed with dichloromethane
  3. custompurified by preparative HPLC (10-90% acetonitrile in water)

Sources & evidence

ORD record
ord-57e548e10f704eb3bcc70eeb19ef8194
Source dataset
uspto-grants-2016_08
Patent number
US09420814B2

Reaction notes

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