2-Amino-3-methylpyridine → 3-Methyl-2-(phthalimidyl)pyridine

HRID 460168Notes

Reaction equation

HRID 460168 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9]([C:14]1[CH:24]=[CH:23][CH:22]=[C:16]2C(N[C:20](=[O:21])[C:15]=12)=O)(OCC)=[O:10]>CN(C=O)C.CCOC(C)=O>[CH3:8][C:7]1[C:2]([N:1]2[C:9](=[O:10])[C:14]3=[CH:24][CH:23]=[CH:22][CH:16]=[C:15]3[C:20]2=[O:21])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 153472-Amino-3-methylpyridineHCID 22254400Ethoxycarbonylphthalimide

Product 1

HCID 106099613-Methyl-2-(phthalimidyl)pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

2-Amino-3-picoline (1.00 mL, 8.62 mmol) was dissolved in DMF (30 mL) at 23° C., and treated with solid carboethoxy-phthalimide (1.89 g, 8.64 mmol), followed by TEA (1.44 mL, 10.3 mmol). The resulting solution was stirred at 23° C. for 15 h. After 15 h, the mixture was diluted with EtOAc (50 mL), and washed with saturated NaCl (1×50 mL), H2O (1×50 mL), dried (MgSO4), and concentrated in vacuo to a yellow solid. Purification over silica gel (0 to 50% EtOAc/Hexanes) provided the title compound as a white solid.

Workup

  1. waitAfter 15 h
  2. washwashed with saturated NaCl (1×50 mL), H2O (1×50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo to a yellow solid
  5. customPurification over silica gel (0 to 50% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-8d249b63a6344341879efa8edcd70f13
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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