3-Pyridinemethanamine → HCID 18353831, compound

HRID 430029Notes

Reaction equation

HRID 430029 reaction equation
C(O[C:4](=[O:18])[CH2:5][O:6][C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1)C.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][NH2:26])[CH:20]=1.C1CCN2C(=NCCC2)CC1>C(O)C>[O:18]=[C:4]([NH:26][CH2:25][C:21]1[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=1)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 310183-PyridinemethanamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10264196HCID 10264196, compound

Product 1

HCID 18353831HCID 18353831, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.9 g (11 mmole) of ethyl 4-(2-ethoxy-2-oxoethoxy)benzoate, 1.4 g (12 mmole) of 3-picolylamine and 2.1 g (1.3 mmole) of DBU were dissolved in ethanol (12 ml), and reaction was then carried out for 24 hours. After the reaction mixture had been concentrated, partition was carried out between ethyl acetate and water. The organic layer was then treated in an ordinary manner to obtain 3.3 g (yield: 90%) of ethyl 4-{2-oxo-2-[(pyridin-3-ylmethyl)amino]ethoxy}benzoate.

Workup

  1. customreaction
  2. concentrationAfter the reaction mixture had been concentrated
  3. custompartition
  4. additionThe organic layer was then treated in an ordinary manner

Sources & evidence

ORD record
ord-c20fbb4bca5b4114bf251fb42f1137cb
Source dataset
uspto-grants-2001_11
Patent number
US06320078B1

Reaction notes

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