Benzyl chloroformate → Benzyl (2-oxo-1,2-dihydropyridin-3-yl)carbamate

HRID 1725630Notes

Reaction equation

HRID 1725630 reaction equation
C(=O)(O)[O-].[Na+].Cl[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[NH2:17][C:18]1[C:19](=[O:24])[NH:20][CH:21]=[CH:22][CH:23]=1>O1CCCC1>[O:24]=[C:19]1[C:18]([NH:17][C:7](=[O:8])[O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:23][CH:22]=[CH:21][NH:20]1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 3223533-Amino-2-pyridinolHCID 516892Sodium Bicarbonate

Product 1

HCID 12045578Benzyl (2-oxo-1,2-dihydropyridin-3-yl)carbamateYield 63.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium bicarbonate (1.70 g, 16.89 mmol) and benzyl chloroformate (1.58 g, 9.29 mmol) were added to a solution of 3-aminopyridin-2(1H)-one (0.930 g, 8.45 mmol) in tetrahydrofuran (20 mL). After 7 h, the mixture was extracted with ethyl acetate and saturated sodium bicarbonate. The organic extract was washed with water and saturated brine, dried over magnesium sulfate, filtered, and concentrated. Purification by chromatography [silica gel, 1% to 5% methanol (10% ammonium hydroxide) in dichloromethane gradient elution] gave the title compound (1.304 g). MS 245 (M+1)

Workup

  1. extractionthe mixture was extracted with ethyl acetate and saturated sodium bicarbonate
  2. extractionThe organic extract
  3. washwas washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification
  8. washby chromatography [silica gel, 1% to 5% methanol (10% ammonium hydroxide) in dichloromethane gradient elution]

Sources & evidence

ORD record
ord-59194e309b1b435bb2578a62c9f5806b
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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