Pyridine → Carbamic acid, 4-pyridinyl-, 4-nitrophenyl ester

HRID 445276

Reaction equation

HRID 445276 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH: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:5]1[CH:6]=[CH:7][C:2]([NH:1][C:9](=[O:10])[O:11][C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 17274-AminopyridineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 10355188Carbamic acid, 4-pyridinyl-, 4-nitrophenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-aminopyridine (1.97 g, 20.9 mmol) in DCM (75 mL) at 0° C. was added 4-nitrophenyl chloroformate (4.21 g, 20.9 mmol) and pyridine (1.7 mL, 20.9 mmol). Then, the mixture was stirred at RT overnight. The white precipitated was filtered off and washed with DCM (2×50 mL), and then dried in vacuo to give the title compound as a white solid, which was used in the next step without further purification. MS (ESI, positive ion) m/z: 260 (M+H).

Workup

  1. customThe white precipitated
  2. filtrationwas filtered off
  3. washwashed with DCM (2×50 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-016b120e0961490a95cef900c506ab88
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Linked notes

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