Ammonia → 2-Amino-6-methoxy-3-nitropyridine

HRID 854067Notes

Reaction equation

HRID 854067 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[NH3:12].[CH3:13][OH:14]>>[NH2:12][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:14][CH3:13])[N:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 38524282-Amino-6-methoxy-3-nitropyridineYield 56.45%

Conditions

Temperature
20 °C

Procedure

2,6-Dichloro-3-nitropyridine, 25.0 gm (0.129 mole) was dissolved in methanol (50.0 ml) at room temperature. To the solution thus obtained, 25.0% aqueous ammonia solution 12.2 ml (0.179 mole) was charged at room temperature. The resulting mixture was heated to 35°–40° C. for 2.0 hrs. The reaction was monitored by TLC. After the completion of the reaction, the mixture was cooled to 20° C. The solid obtained was washed, filtered with methanol and dried to yield 12.50 gm of 2-amino-6-methoxy-3-nitro pyridine (56.45%) with the HPLC purity of 99.3%: Melting point 192°–195° C.; 1HNMR: (DMSO D6) δ6.75–6.77 ppm (d, 1H), δ8.38–8.40 (d, 1H).

Workup

  1. customTo the solution thus obtained
  2. temperatureThe resulting mixture was heated to 35°–40° C. for 2.0 hrs
  3. customAfter the completion of the reaction
  4. customThe solid obtained
  5. washwas washed
  6. filtrationfiltered with methanol
  7. customdried

Sources & evidence

ORD record
ord-6baf5fde0ee04a6bbf12b505fd57da3b
Source dataset
uspto-grants-2007_08
Patent number
US07256295B2

Reaction notes

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