Ethanolamine → 2-Chloro-6-(2-hydroxyethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

HRID 1799545Notes

Reaction equation

HRID 1799545 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8]Cl)[C:5]([C:10]([O:12]C)=O)=[CH:4][CH:3]=1.[CH2:14]([CH2:16][NH2:17])[OH:15]>CO>[Cl:1][C:2]1[N:7]=[C:6]2[CH2:8][N:17]([CH2:16][CH2:14][OH:15])[C:10](=[O:12])[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 700Ethanolamine3×HCID 59525762Methyl 6-chloro-2-(chloromethyl)pyridine-3-carboxylate

Product 1

HCID 582166462-Chloro-6-(2-hydroxyethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 6-chloro-2-(chloromethyl)pyridine-3-carboxylate (0.1 g, 0.45 mmol) and ethanolamine (0.11 mL, 1.82 mmol) were stirred in MeOH (10 mL) at room temperature overnight. Additional ethanolamine (0.11 mL, 1.82 mmol) was added and stirring continued for 8 hours. Additional ethanolamine (0.22 mL, 3.64 mmol) was then added and stirring continued for 3 days. The solvent was removed in vacuo and the residue purified by silica gel chromatography (0-5% MeOH/EtOAc) to give the title compound as a white solid.

Workup

  1. stirringstirring
  2. waitcontinued for 3 days
  3. customThe solvent was removed in vacuo
  4. customthe residue purified by silica gel chromatography (0-5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-87509003de184f31a930ef55e7722664
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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