Hydrochloric Acid → 2-Amino-5-methoxy-4-(3-morpholinopropoxy)benzamide

HRID 855676Notes

Reaction equation

HRID 855676 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:5]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O: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]>[NH2:13][C:7]1[CH:6]=[C:5]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O: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 216992855-Methoxy-4-(3-morpholinopropoxy)-2-nitrobenzamide2×

Product 1

HCID 216992712-Amino-5-methoxy-4-(3-morpholinopropoxy)benzamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Concentrated hydrochloric acid (30 ml) was added to a suspension of 5-methoxy-4-(3-morpholinopropoxy)-2-nitrobenzamide (5.67 g) in methanol (150 ml) and the mixture was heated to 60° C. When the 5-methoxy-4-(3-morpholinopropoxy)-2-nitrobenzamide had dissolved, iron powder (5.6 g, 100 mmol) was added in portions to the reaction mixture which was then heated for 90 minutes. After cooling, the insolubles were removed by filtration through diatomaceous earth, the volatiles were removed from the filtrate by evaporation and the residue was purified on a Diaion (trade mark of Mitsubishi) HP20SS resin column, eluting with water and then with hydrochloric acid (pH2). Concentration of the fractions by evaporation gave a precipitate which was collected by filtration and dried under vacuum over phosphorus pentoxide to give 2-amino-5-methoxy-4-(3-morpholinopropoxy)benzamide as a hydrochloride salt 4.67 g, 75%) as beige crystals.

Workup

  1. temperaturewas then heated for 90 minutes
  2. temperatureAfter cooling
  3. customthe insolubles were removed by filtration through diatomaceous earth
  4. customthe volatiles were removed from the filtrate by evaporation
  5. customthe residue was purified on a Diaion (trade mark of Mitsubishi) HP20SS resin column
  6. washeluting with water
  7. customConcentration of the fractions by evaporation
  8. customgave a precipitate which
  9. filtrationwas collected by filtration
  10. dry with materialdried under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-69b500fa916448f9aa0a10fb9e082a7e
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

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