Hexane → 2-(N-Boc-Amino)-3-methylpyridine

HRID 505672Notes

Reaction equation

HRID 505672 reaction equation
C(O[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(C)(C)C.CCCCCC.[NH2:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=1>C(OCC)(=O)C>[CH3:26][C:25]1[C:20]([NH:19][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[N:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 8058Hexane2×HCID 153472-Amino-3-methylpyridineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 117458482-(N-Boc-Amino)-3-methylpyridineYield 64.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To di t-butylcarbonate (32.29 g, 147.95 mmol) was added hexane (35 ml) and the solution was refluxed under heating at 80° C. Under refluxing, 2-amino-3-methylpyridine (10.00 g, 92.47 mmol) in ethyl acetate (10 ml) was dropped in a period of 15 minutes. After the mixture was refluxed for 2 hours and cooled to room temperature, thereto was added hexane (20 ml). The resulting crystals were filtered and dried in vacuo to give the subject compound (12.39 g, 64%).

Workup

  1. temperaturethe solution was refluxed
  2. temperatureUnder refluxing
  3. temperatureAfter the mixture was refluxed for 2 hours
  4. temperaturecooled to room temperature
  5. filtrationThe resulting crystals were filtered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-be26d010eee1401b83f7eaa97f9a1338
Source dataset
uspto-grants-2010_08
Patent number
US07781479B2

Reaction notes

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