Pyridine → Phenyl pyridin-3-ylcarbamate

HRID 1429678Notes

Reaction equation

HRID 1429678 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.N1C=CC=CC=1.Cl[C:15]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16]>CC#N>[C:18]1([O:17][C:15](=[O:16])[NH:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 100093-AminopyridineHCID 15891Phenyl chloroformate

Product 1

HCID 6935890Phenyl pyridin-3-ylcarbamateYield 80.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution consisting of pyridin-3-yl amine (9.49 g, 101 mmol) and pyridine (8.77 g, 111 mmol) in CH3CN (80 mL) at 0° C. was added phenyl chloroformate (15.8 g, 101 mmol) dropwise. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction was quenched with H2O (200 mL) and the resulting precipitate was filtered and dried under vacuum to provide the title compound as a tan solid (17.34 g, 80%). MS (ESI+): calcd for C12H10N2O2 m/z 214.07, found 215.3 (M+H)+. 1H NMR (500 MHz, d6-DMSO): 10.46 (s, 1H), 8.69 (d, J=2.4 Hz, 1H), 8.27 (dd, J=4.7, 1.4 Hz, 1H), 7.93 (d, J=8.4 Hz, 1H), 7.47-7.41 (m, 2H), 7.37 (dd, J=8.4, 4.7 Hz, 1H), 7.31-7.22 (m, 3H).

Workup

  1. customThe reaction was quenched with H2O (200 mL)
  2. filtrationthe resulting precipitate was filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-239d0658f8d6457f966b084b43afd751
Source dataset
uspto-grants-2015_01
Patent number
US08940745B2

Reaction notes

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