Ammonium Hydroxide → 6-Bromo-5-methoxypyridin-2-amine

HRID 583180Notes

Reaction equation

HRID 583180 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([N+:10]([O-])=O)[N:3]=1.[OH-].[NH4+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>CCCCCC.C(OCC)(=O)C.O.C(O)C>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([NH2:10])[N:3]=1

Participants

7

Reactant 3

HCID 14923Ammonium HydroxideHCID 24489Sodium DithioniteHCID 126928732-Bromo-3-methoxy-6-nitropyridine

Product 1

HCID 127582096-Bromo-5-methoxypyridin-2-amineYield 50%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
60 °C

Procedure

2-Bromo-3-methoxy-6-nitropyridine (470 mg, 2.0 mmol) was added to 8 mL (3:1 water: ethanol) and 2 mL of 30% ammonium hydroxide. Added 350 mg (2 mmol) of sodium hydrosulfite (Na2SsO4) and heated to 60° C. After 30 min, no starting material was seen. Added 50 mL of water and extracted the product with methylene chloride (2×25 mL). Dried over MgSO4, filtered and reduced the volume. Flash chromatography (75/25 hexane/ethyl acetate) recovered 200 mg of product (50% yield). 1H NMR (CDCl3, 200 MHz) δ 7.06 (d, 1H, 10 Hz), 6.41 (d, 1H, J=10 Hz), 3.8 (s, 3H) ppm

Workup

  1. extractionextracted the product with methylene chloride (2×25 mL)
  2. dry with materialDried over MgSO4
  3. filtrationfiltered

Sources & evidence

ORD record
ord-4ca2a55c909848c791a3cd71e19db04a
Source dataset
uspto-grants-1999_07
Patent number
US05929094

Reaction notes

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