Acetic Acid → 6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo(3,4-b)pyrazin-5-one

HRID 1876772Notes

Reaction equation

HRID 1876772 reaction equation
CN1CCN(C([O:10][CH:11]2[N:20]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][N:26]=3)[C:18](=[O:19])[C:13]3[N:14]=[CH:15][CH:16]=[N:17][C:12]2=3)=O)CC1.C(O)(=O)C.Cl.Br>O.C(O)=O>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([N:20]2[CH:18]([OH:19])[C:13]3[C:12](=[N:17][CH:16]=[CH:15][N:14]=3)[C:11]2=[O:10])=[N:26][CH:25]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 5735Zopiclone

Product 1

HCID 64519726-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo(3,4-b)pyrazin-5-one

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

According to the present invention, (R) or (S) Zopiclone is treated with acid selected from acetic acid, formic acid, hydrochloric acid, hydrobromic acid or mixtures thereof; the resulting solution is heated between 50° to 70° C. followed by cooling and diluting with water to give 6-(5-chloropyridin-2-yl)-5-hydroxy-7-oxo-5,6-dihydro pyrrolo-[3,4-b]-pyrazine. This intermediate is used for the preparation of Zopiclone by conventional method.

Workup

  1. additionis treated with acid
  2. temperaturethe resulting solution is heated between 50° to 70° C.
  3. temperatureby cooling

Sources & evidence

ORD record
ord-9c728b54f80f4db1a201f83f2df7379c
Source dataset
uspto-grants-2012_11
Patent number
US08309723B2

Reaction notes

Loading…