Acetic Acid → HCID 19701935, compound

HRID 862141Notes

Reaction equation

HRID 862141 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:21]([O-])=O)=[C:6]([CH:20]=1)[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]2[O:17][CH2:18][O:19][C:13]=2[CH:12]=1)=[O:8].C(O)(=O)C.O>[Fe].C(O)C>[NH2:21][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20][C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]2[O:17][CH2:18][O:19][C:13]=2[CH:12]=1)=[O:8]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 898773HCID 898773, compound

Product 1

HCID 19701935HCID 19701935, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

5-Chloro-N-(3,4-methylenedioxybenzyl)-2-nitrobenzamide (620 mg), acetic acid (1 ml), water (1 ml) and ethanol (20 ml) were mildly heated together under reflux, followed by the addition of 1.0 g of powdered iron in portions under stirring. The obtained mixture was refluxed for one hour and filtered under heating to remove brown insolubles. The filtrate was concentrated, followed by the addition of ethanol. The resulting mixture was dissolved by heating. Concentrated hydrochloric acid was added to the obtained solution in portions, by which the brown solution turned yellow and transparent. This yellow transparent solution was seeded to give crystals. The resulting mixture was cooled and filtered to recover the crystals. The crystals were washed with ethanol and ether and dried to give 520 mg of 2-amino-5-chloro-N-(3,4-methylenedioxybenzyl)benzamide.

Workup

  1. temperatureunder reflux
  2. temperatureThe obtained mixture was refluxed for one hour
  3. filtrationfiltered
  4. temperatureunder heating
  5. customto remove brown insolubles
  6. concentrationThe filtrate was concentrated
  7. additionfollowed by the addition of ethanol
  8. dissolutionThe resulting mixture was dissolved
  9. temperatureby heating
  10. additionConcentrated hydrochloric acid was added to the obtained solution in portions, by which the brown solution
  11. customto give crystals
  12. temperatureThe resulting mixture was cooled
  13. filtrationfiltered
  14. customto recover the crystals
  15. washThe crystals were washed with ethanol and ether
  16. customdried

Sources & evidence

ORD record
ord-dea26a806f9a4c87a75ae832a9ccb228
Source dataset
uspto-grants-1998_02
Patent number
US05716993

Reaction notes

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