Pyridine → 4-Nitrophenyl pyridin-2-ylcarbamate

HRID 445274Notes

Reaction equation

HRID 445274 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[C:9]([O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=[O:10].N1C=CC=CC=1>C(Cl)Cl>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:9](=[O:10])[O:11][C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 104392-AminopyridineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 103327734-Nitrophenyl pyridin-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-aminopyridine (2.0 mL, 21.25 mmol) in DCM (35 mL) at 0° C. was added a solution of 4-nitrophenyl chloroformate (4.28 g, 21.25 mmol) in DCM (35 mL) and pyridine (1.73 mL, 21.25 mmol, anhydrous). After the addition was completed, the reaction mixture was stirred at RT for 16 h under an atmosphere of nitrogen. A white precipitated was observed and it was collected by filtration. The filtrate was washed with DCM (3×50 mL) to give the title compound as a white solid. MS (ESI, positive ion) m/z: 260 (M+H).

Workup

  1. additionAfter the addition
  2. customA white precipitated
  3. filtrationit was collected by filtration
  4. washThe filtrate was washed with DCM (3×50 mL)

Sources & evidence

ORD record
ord-d0f794324293478fb05355930b282435
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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