Pyridine → 4-Nitrophenyl (5-chloropyridin-2-yl)carbamate

HRID 1796218Notes

Reaction equation

HRID 1796218 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.N1C=CC=CC=1.Cl[C:16]([O:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)=[O:17]>C(Cl)Cl>[N+:25]([C:22]1[CH:21]=[CH:20][C:19]([O:18][C:16](=[O:17])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=2)=[CH:24][CH:23]=1)([O-:27])=[O:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 661742-Amino-5-chloropyridineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 574289294-Nitrophenyl (5-chloropyridin-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Amino-5-chloropyridine (1.05 g, 8.2 mmol) was suspended in 15 mL dry DCM under Ar, added dry pyridine (0.66 mL, 8.2 mmol), cooled to 0° C. and added 4-nitrophenol chloroformate. A white precipitate forms rapidly. Stirred at ambient temperature for 1 hour, filtered off solid, washed with water and then DCM. A white solid recovered which is consistent with title compound. (2.1 g, 88%) 1H-NMR (D6-DMSO)

Workup

  1. filtrationfiltered off solid
  2. washwashed with water
  3. customA white solid recovered which

Sources & evidence

ORD record
ord-6d18e5e60f1f476eb710828701a5bf62
Source dataset
uspto-grants-2006_04
Patent number
US07030141B2

Reaction notes

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