Methylamine → 2-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

HRID 2060613Notes

Reaction equation

HRID 2060613 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.[CH3:14][NH2:15].O1CCCC1>O>[Cl:1][C:2]1[N:7]=[C:6]2[CH2:8][N:15]([CH3:14])[C:10](=[O:12])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 59525762Methyl 6-chloro-2-(chloromethyl)pyridine-3-carboxylate

Product 1

HCID 582166242-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 6-chloro-2-(chloromethyl)pyridine-3-carboxylate (1.5 g, 6.82 mmol) was stirred in a solution of methylamine in tetrahydrofuran (35 mL, 70.0 mmol) at room temperature overnight. Water was added and the products extracted into ethyl acetate (2×). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was triturated in diethyl ether to give a first batch of product. The mother liquor was concentrated in vacuo and the residue purified by flash chromatography (silica, 40-100% ethyl acetate/hexanes) and combined with the first batch to afford the title compound as a white solid. LRMS (APCI) calcd for C8H8ClN2O [M+H]+ 183.0, found 183.0.

Workup

  1. extractionthe products extracted into ethyl acetate (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated in diethyl ether
  6. customto give a first batch of product
  7. concentrationThe mother liquor was concentrated in vacuo
  8. customthe residue purified by flash chromatography (silica, 40-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-91a7aefdc8f04d099a0a3cba0ce7282e
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

Loading…