Hydrochloric Acid → 4-Amino-N-(1-azabicyclo[2.2.2]octan-3-yl)-5-chloro-2-hydroxybenzamide

HRID 1086055Notes

Reaction equation

HRID 1086055 reaction equation
C([S-])C.[Na+].[NH2:5][C:6]1[C:22]([Cl:23])=[CH:21][C:9]([C:10]([NH:12][CH:13]2[CH:18]3[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]3)[CH2:14]2)=[O:11])=[C:8]([O:24]C)[CH:7]=1.Cl>CN(C=O)C>[NH2:5][C:6]1[C:22]([Cl:23])=[CH:21][C:9]([C:10]([NH:12][CH:13]2[CH:18]3[CH2:17][CH2:16][N:15]([CH2:20][CH2:19]3)[CH2:14]2)=[O:11])=[C:8]([OH:24])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 108182ZacoprideHCID 4459711Sodium ethanethiolate

Product 1

HCID 156708204-Amino-N-(1-azabicyclo[2.2.2]octan-3-yl)-5-chloro-2-hydroxybenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of sodium ethanethiolate in DMF is added 4-amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxybenzamide and the mixture heated under reflux to 1 h. After cooling, the mixture is neutralized with hydrochloric acid, concentrated in vacuo and the residue purified by chromatography to give the title compound.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux to 1 h
  3. temperatureAfter cooling
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-ec78b7e2ac9240879079fac9e71ab000
Source dataset
uspto-grants-1991_04
Patent number
US05011992

Reaction notes

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