Formaldehyde → (5-Iodopyridin-2-yl)-methylene-amine

HRID 751272Notes

Reaction equation

HRID 751272 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1.[CH2:9]=O>FC(F)(F)C(O)=O>[I:8][C:5]1[CH:6]=[CH:7][C:2]([N:1]=[CH2:9])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 885792-Pyridinamine, 5-iodo-

Product 1

HCID 58611975(5-Iodopyridin-2-yl)-methylene-amineYield 76.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidCatalyst

Procedure

Add trifluoroacetic acid (3 drops) to a suspension of 2-amino-5-iodopyridine (1.0 g, 4.5 mmol) and paraformaldehyde (1.0 g). Heat the mixture at reflux for 15 h and concentrate. Purification by flash chromatography eluting with ethyl acetate gives 0.8 g (75%) of the title compound as a white solid. ES+ m/e 232.6 (M+1).

Workup

  1. temperatureHeat the mixture
  2. temperatureat reflux for 15 h
  3. concentrationconcentrate
  4. customPurification by flash chromatography
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-c30ff42efef54040ada30ab2e70ed825
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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