Hydrochloric Acid → HCID 178508042, compound

HRID 547383Notes

Reaction equation

HRID 547383 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:27])C=1.Cl>CC(C)=O>[NH2:1][C:2]1[C:7]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 70297m-Chloroperbenzoic acidHCID 13451701Benzyl (2-aminopyridin-3-yl)carbamate

Product 1

HCID 178508042HCID 178508042, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of benzyl (2-aminopyridin-3-yl)carbamate in acetone was added a solution of m-chloro perbenzoic acid in acetone and the suspension was stirred at room temperature. After 2 hours the suspension was cooled to 0° C., HCl (2N in Et2O) was added, and the precipitate filtered. To the precipitate was added saturated aqueous NaHCO3, EtOAc and MeOH and the mixture stirred until dissolution. The solution was evaporated and the residue washed with water until the pH of the filtrate was neutral. The solid was dried under vacuum.

Workup

  1. temperatureAfter 2 hours the suspension was cooled to 0° C.
  2. filtrationthe precipitate filtered
  3. additionTo the precipitate was added saturated aqueous NaHCO3, EtOAc and MeOH
  4. stirringthe mixture stirred until dissolution
  5. customThe solution was evaporated
  6. washthe residue washed with water until the pH of the filtrate
  7. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-4b8f859f683c49b9ad974d223eaa024d
Source dataset
uspto-grants-2011_05
Patent number
US07939537B2

Reaction notes

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