Réaction #670362

ord-4ca2a55c909848c791a3cd71e19db04a

Équation de réaction

COc1ccc([N+](=O)[O-])nc1Br
2-Bromo-3-methoxy-6-nitropyridine
[NH4+].[OH-]
ammonium hydroxide
O=S([O-])S(=O)[O-].[Na+].[Na+]
sodium hydrosulfite
→
COc1ccc(N)nc1Br
product
Rendement 50.0%
COc1ccc(N)nc1Br
2-Bromo-3-methoxy-6-aminopyridine
Rendement 50.0%

Réactifs

COc1ccc([N+](=O)[O-])nc1Br
2-Bromo-3-methoxy-6-nitropyridine
[NH4+].[OH-]
ammonium hydroxide
O=S([O-])S(=O)[O-].[Na+].[Na+]
sodium hydrosulfite

Réactifs

Aucun

Solvants

CCO
ethanol
O
water
CCCCCC.CCOC(C)=O
hexane ethyl acetate
O
water

Conditions de réaction

Température
60°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Extractionextracted the product with methylene chloride (2×25 mL)
  2. 2
    SéchageDried over MgSO4
  3. 3
    Filtrationfiltered

Mode opératoire

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

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05929094uspto-grants-1999_07