Hydrochloric Acid → Methyl 2-(2'-carbamoylbiphenyl-4-yl)methylamino-3-nitrobenzoate

HRID 1707717Notes

Reaction equation

HRID 1707717 reaction equation
C(OC([N:8]([C:25]1[C:34]([N+:35]([O-:37])=[O:36])=[CH:33][CH:32]=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22](=[O:24])[NH2:23])=[CH:12][CH:11]=1)=O)(C)(C)C.Cl>CO>[C:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:13]1[CH:12]=[CH:11][C:10]([CH2:9][NH:8][C:25]2[C:34]([N+:35]([O-:37])=[O:36])=[CH:33][CH:32]=[CH:31][C:26]=2[C:27]([O:29][CH3:30])=[O:28])=[CH:15][CH:14]=1)(=[O:24])[NH2:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54203098Methyl 2-[N-tert-butoxycarbonyl-N-(2'-carbamoylbiphenyl-4-yl)methylamino]-3-nitrobenzoate

Product 1

HCID 18693154Methyl 2-(2'-carbamoylbiphenyl-4-yl)methylamino-3-nitrobenzoateYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the compound (2.8 g) obtained in Example (54b) in methanol (15 ml) and 1N-HCl (6 ml) was heated for 2 hours under reflux. After removal of the solvent, the residue was made alkaline with an aqueous solution of NaHCO3, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over MgSO4 and concentrated to dryness. The residue was purified by column chromatography on silica gel, and the product was recrystallized from ethyl acetate-hexane to afford yellow needles (1.6 g, 73%).

Workup

  1. temperaturewas heated for 2 hours
  2. temperatureunder reflux
  3. customAfter removal of the solvent
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by column chromatography on silica gel
  9. customthe product was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-20ed5e28413646f0a53adf21edc008f1
Source dataset
uspto-grants-1994_10
Patent number
US05354766

Reaction notes

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