2-Pyridinamine, 5-iodo- → 2-Amino-5-methoxypyridine

HRID 1287487Notes

Reaction equation

HRID 1287487 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[CH3:9][O-:10].[Na+]>[Cu].CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:10][CH3:9])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 885792-Pyridinamine, 5-iodo-HCID 10942334Sodium Methoxide

Product 1

HCID 113209342-Amino-5-methoxypyridine

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent

Procedure

2-Amino-5-methoxypyridine is prepared by combining 55 g. of 2-amino-5-iodopyridine, 20 g. of sodium methoxide, 5 g. of copper powder, 500 ml. of methanol in a glass lined bomb and rocking at 150° C. for 12 hours. Upon concentration to dryness, an extraction with chloroform extracts are dried and evaporated to dryness in vacuo. The residue is chromatographed on 1200 g. of silica gel eluting with 50% ethylacetate and methylenechloride affording 2-amino-5-methoxy pyridine.

Workup

  1. custom2-Amino-5-methoxypyridine is prepared
  2. customat 150° C.
  3. customfor 12 hours
  4. concentrationUpon concentration to dryness
  5. extractionan extraction with chloroform extracts
  6. customare dried
  7. customevaporated to dryness in vacuo
  8. customThe residue is chromatographed on 1200 g

Sources & evidence

ORD record
ord-ac015bd96fc3400e9b208c7ae9093ccb
Source dataset
uspto-grants-1976_10
Patent number
US03984549

Reaction notes

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