Hydrochloric Acid → 6-Chloro-5-methoxypyridin-3-amine

HRID 1680392Notes

Reaction equation

HRID 1680392 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N+:10]([O-])=O)=[CH:4][N:3]=1.Cl.[OH-].[Na+]>>[NH2:10][C:5]1[CH:6]=[C:7]([O:8][CH3:9])[C:2]([Cl:1])=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 234561522-Chloro-3-methoxy-5-nitropyridine

Product 1

HCID 234561436-Chloro-5-methoxypyridin-3-amine

Conditions

Temperature
5 °C

Procedure

2-Chloro-3-methoxy-5-nitropyridine (1.5 g, 0.008 mole) was added to concentrated hydrochloric acid (15 ml) at 5° C., followed by stannous chloride (5.0 g). The reaction mixture was stirred for 10 minutes at 5° C., heated for 30 minutes on a steam bath, cooled, neutralized with aqueous sodium hydroxide (20 percent by weight) and extracted with 1,1,1-trichloroethane. The trichloroethane extract was dried over MgSO4 and evaporated in vacuo to yield a white solid; yield, 1.02 g (91 percent), m.p. 93° to 94° C.

Workup

  1. temperatureheated for 30 minutes on a steam bath
  2. temperaturecooled
  3. extractionextracted with 1,1,1-trichloroethane
  4. extractionThe trichloroethane extract
  5. dry with materialwas dried over MgSO4
  6. customevaporated in vacuo
  7. customto yield a white solid
  8. customyield

Sources & evidence

ORD record
ord-5ed74b75c462448d8c985d472fbc5161
Source dataset
uspto-grants-1981_06
Patent number
US04273706

Reaction notes

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