Hydrochloric Acid → HCID 178441478, compound

HRID 653699Notes

Reaction equation

HRID 653699 reaction equation
Cl.[N+:2]([C:5]1[C:6]([NH:15][C:16](=O)[CH2:17][CH2:18][CH2:19][CH3:20])=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])([O-])=O>[Fe].CO>[CH2:17]([C:16]1[NH:15][C:6]2[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=[CH:14][C:5]=2[N:2]=1)[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15291136Methyl 3-nitro-2-(pentanoylamino)benzoate

Product 1

HCID 178441478HCID 178441478, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a mixture of conc. HCl (5.3 ml) and methanol (35 ml) was added methyl 3-nitro-2-(N-valerylamino)benzoate (2.8 g), to which was added iron powder (1.7 g) in portions while stirring at room temperature. The resultant mixture was heated for 8 hours under reflux. Insoluble material was filtered off, and the filtrate was concentrated. To the concentrate were added water and ethyl acetate. The aqueous layer was made basic with 6N NaOH and was extracted with ethyl acetate. The organic layers were combined, washed with water and dried. The solvent was evaporated, and the residue was purified by column chromatography on silica gel. The crystals thus obtained were recrystallized from isopropyl ether to give colorless needles (1.6 g, 70%), m.p. 97°-98° C.

Workup

  1. temperatureunder reflux
  2. filtrationInsoluble material was filtered off
  3. concentrationthe filtrate was concentrated
  4. additionTo the concentrate were added water and ethyl acetate
  5. extractionwas extracted with ethyl acetate
  6. washwashed with water
  7. customdried
  8. customThe solvent was evaporated
  9. customthe residue was purified by column chromatography on silica gel
  10. customThe crystals thus obtained
  11. customwere recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-496810bfe0c243a28849e43705835304
Source dataset
uspto-grants-1992_07
Patent number
US05128356

Reaction notes

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