Ammonium Chloride → 2-Amino-3-(2-methoxycarbonylamino-6-methylbenzyloxy)pyridine

HRID 1762187Notes

Reaction equation

HRID 1762187 reaction equation
[Cl-].[NH4+].[CH3:3][O:4][C:5]([NH:7][C:8]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:9]=1[CH2:10][O:11][C:12]1[C:13]([N+:18]([O-])=O)=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:6]>O.C(O)C.[Fe]>[NH2:18][C:13]1[C:12]([O:11][CH2:10][C:9]2[C:21]([CH3:25])=[CH:22][CH:23]=[CH:24][C:8]=2[NH:7][C:5]([O:4][CH3:3])=[O:6])=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 143684013-(2-Methoxycarbonylamino-6-methylbenzyloxy)-2-nitropyridine

Product 1

HCID 200425332-Amino-3-(2-methoxycarbonylamino-6-methylbenzyloxy)pyridine

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of iron powder (2.76 g) and ammonium chloride (0.275 g) in water (19 ml) and ethanol (63 ml) was added portionwise 3-(2-methoxycarbonylamino-6-methylbenzyloxy)-2-nitropyridine (6.27 g) under reflux and then stirred for an additional 30 minutes. The hot mixture was filtered by suction and the filtrate was made alkaline with sodium bicarbonate and evaporated in vacuo. The residue was washed with water, dried, and recrystallized from ethyl acetate to give 2-amino-3-(2-methoxycarbonylamino-6-methylbenzyloxy)pyridine.

Workup

  1. temperatureunder reflux
  2. filtrationThe hot mixture was filtered by suction
  3. customevaporated in vacuo
  4. washThe residue was washed with water
  5. customdried
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fa560c57532a489b988757d53d396939
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

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