Water → HCID 47148542, compound

HRID 843716Notes

Reaction equation

HRID 843716 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:15][O:16][C:17]([CH2:19][CH2:20][C:21](Cl)=[O:22])=[O:18].O>ClCCl>[CH3:15][O:16][C:17](=[O:18])[CH2:19][CH2:20][C:21]([NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 100093-AminopyridineHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl ester

Product 1

HCID 47148542HCID 47148542, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-aminopyridine (1 g) in dichloromethane (10 ml) was added triethylamine (1.63 ml) and 3-methoxycarbonylpropionyl chloride (1.44 ml) under stirring at 0° C. After stirring at ambient temperature for 1 hour, the mixture was poured into water and extracted with dichloromethane. The extract was washed with water, saturated aqueous NaHCO3 solution, water and brine, and dried over MgSO4, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with (CHCl3:MeOH=100:1), and recrystallized from diethyl ether to give N-(3-pyridyl)succinamic acid methyl ester (0.73 g).

Workup

  1. stirringAfter stirring at ambient temperature for 1 hour
  2. extractionextracted with dichloromethane
  3. washThe extract was washed with water, saturated aqueous NaHCO3 solution, water and brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with (CHCl3:MeOH=100:1)
  7. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-7dd3d45589b24c4fad0b26db209cf354
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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