Ammonium Chloride → Benzyl 2,3-diaminobenzoate

HRID 2423244Notes

Reaction equation

HRID 2423244 reaction equation
[Cl-].[NH4+].[NH2:3][C:4]1[C:19]([N+:20]([O-])=O)=[CH:18][CH:17]=[CH:16][C:5]=1[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]>[Fe].C(O)C.O>[NH2:3][C:4]1[C:19]([NH2:20])=[CH:18][CH:17]=[CH:16][C:5]=1[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67244884Benzyl 2-amino-3-nitrobenzoate

Product 1

HCID 57780629Benzyl 2,3-diaminobenzoateYield 97.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

Iron powder (0.78 g) and ammonium chloride (0.15 g) were added in that order to an ethanol/water (4/1) solution (40 mL) of benzyl 2-amino-3-nitrobenzoate (0.38 g), and this was heated under reflux for 20 minutes with vigorous stirring. The insoluble matter was separated by filtration while hot, and the filtrate was evaporated under reduced pressure to about ⅕, and then aqueous sodium hydrogencarbonate solution was added, followed by extraction with ethyl acetate. The organic layer was washed with water, dried, and evaporated under reduced pressure to obtain benzyl 2,3-diaminobenzoate (0.33 g).

Workup

  1. temperaturethis was heated
  2. temperatureunder reflux for 20 minutes with vigorous stirring
  3. customThe insoluble matter was separated by filtration while hot, and the filtrate
  4. customwas evaporated under reduced pressure to about ⅕
  5. additionaqueous sodium hydrogencarbonate solution was added
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with water
  8. customdried
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ad1e158b50164137bff08822e6bae64b
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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