Hydrochloric Acid → 2-Amino-5-methoxy-4-(3-(pyrrolidin-1-yl)propoxy)benzamide hydrochloride

HRID 454008Notes

Reaction equation

HRID 454008 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[C:5]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:6][C:7]([N+:13]([O-])=O)=[C:8]([CH:12]=1)[C:9]([NH2:11])=[O:10]>CO.[Fe]>[ClH:1].[NH2:13][C:7]1[CH:6]=[C:5]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:4]([O:3][CH3:2])=[CH:12][C:8]=1[C:9]([NH2:11])=[O:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 218748225-Methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzamide

Product 1

HCID 218748202-Amino-5-methoxy-4-(3-(pyrrolidin-1-yl)propoxy)benzamide hydrochlorideYield 85%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Concentrated hydrochloric acid (5 ml) was added to a suspension of 5-methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzamide (1.5 g, 4.64 mmol) in methanol (20 ml) and the mixture was heated at 50° C. to give a solution. Iron powder (1.3 g, 23.2 mmol) was added in portions and the reaction mixture was then heated at reflux for 1 hour. The mixture was allowed to cool, the insolubles were removed by filtration through diatomaceous earth and the volatiles were removed from the filtrate by evaporation. The residue was purified on a Diaion (trade mark of Mitsubishi) HP20SS resin column, eluting with water and then with dilute hydrochloric acid (pH2). The fractions containing product were concentrated by evaporation and the resulting precipitate was collected by filtration and dried under vacuum over phosphorus pentoxide to give 2-amino-5-methoxy-4-(3-(pyrrolidin-1-yl)propoxy)benzamide hydrochloride (1.44 g, 85%).

Workup

  1. customto give a solution
  2. temperaturethe reaction mixture was then heated
  3. temperatureat reflux for 1 hour
  4. temperatureto cool
  5. customthe insolubles were removed by filtration through diatomaceous earth
  6. customthe volatiles were removed from the filtrate by evaporation
  7. customThe residue was purified on a Diaion (trade mark of Mitsubishi) HP20SS resin column
  8. washeluting with water
  9. additionThe fractions containing product
  10. concentrationwere concentrated by evaporation
  11. filtrationthe resulting precipitate was collected by filtration
  12. dry with materialdried under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-2fceccc769624f6e89fe173681259589
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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