Ethanol → 2-Amino-3-methoxypyridine

HRID 1266939Notes

Reaction equation

HRID 1266939 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:9]([O-])=O)=[N:5][CH:6]=[CH:7][CH:8]=1.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[SH-].C(O)C>O.C1(C)C=CC=CC=1>[NH2:9][C:4]1[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 5560633-Methoxy-2-nitropyridineHCID 162115161313-84-4

Product 1

HCID 99203842-Amino-3-methoxypyridineYield 70.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Then, a reaction flask was loaded with this 3-methoxy-2-nitropyridine (9.0 g), sodium sulfide enneahydrate (64 g), ethanol (93 ml) and water (46 ml) and they were mixed, followed by stirring at 70° C. for 2.5 hours. Then, the mixture was cooled to room temperature. To this, toluene and water were added, followed by stirring. The organic layer was collected and washed with a saline solution, and then dried with sodium sulfate. This was filtrated and the filtrate was condensed to give 2-amino-3-methoxypyridine (5.1 g).

Workup

  1. additionwere mixed
  2. temperatureThen, the mixture was cooled to room temperature
  3. stirringby stirring
  4. customThe organic layer was collected
  5. washwashed with a saline solution
  6. dry with materialdried with sodium sulfate
  7. filtrationThis was filtrated
  8. customcondensed

Sources & evidence

ORD record
ord-5ffa6e064cb244a3a4d125a5a4d4c577
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Reaction notes

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