2-Aminopyridine → Phenyl pyridin-2-ylcarbamate

HRID 1754187Notes

Reaction equation

HRID 1754187 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][CH:15]=[CH:14][CH:13]=1)=[O:10]>C1COCC1.CCOC(C)=O>[C:12]1([O:11][C:9](=[O:10])[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 104392-AminopyridineHCID 15891Phenyl chloroformate2×

Product 1

HCID 11138456Phenyl pyridin-2-ylcarbamateYield 124.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-aminopyridine (3.0 g) in dry THF (30 mL) was added phenyl chloroformate (1.0 g, 0.8 mL) dropwise at 0° C., followed by another batch of phenyl chloroformate (1.0 g, 0.8 mL). The reaction mixture was allowed to warm to rt. After 18 h, the mixture was diluted with EtOAc (100 mL) and washed with satd. aq. NaHCO3 (20 mL). The organic layer was dried (MgSO4) and concentrated. The residue was chromatographed to give a white solid (1.7 g).

Workup

  1. washwashed with satd
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was chromatographed

Sources & evidence

ORD record
ord-7f1ea2586341483ca4ada067e4f72bb2
Source dataset
uspto-grants-2015_10
Patent number
US09169224B2

Reaction notes

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