Iodoethane → Ethyl 3-amino-4-propylpyridine-2-carboxylate

HRID 232567Notes

Reaction equation

HRID 232567 reaction equation
[NH2:1][C:2]1[C:3]([C:11]([OH:13])=[O:12])=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:20](I)[CH3:21]>O>[NH2:1][C:2]1[C:3]([C:11]([O:13][CH2:20][CH3:21])=[O:12])=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 224623913-Amino-4-n-propylpyridine-2-carboxylic acid

Product 1

HCID 22462380Ethyl 3-amino-4-propylpyridine-2-carboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Amino-4-n-propylpyridine-2-carboxylic acid (Preparation 4; 0.36 g, 0,002 mol) was added to a stirred mixture of cesium carbonate (0,325 g, 0.001 mol) in water (20 ml), then this mixture was evaporated under vacuum and the residue azeotroped with dimethylformamide (2×20 ml). The resulting cesium salt was suspended in dimethylformamide (3 ml) and the stirred suspension then treated dropwise with ethyl iodide (0.17 ml, 0.0021 mol). After a further 0.25 hour, the solvent was evaporated under vacuum and the residue partitioned between water (20 ml) and ethyl acetate (20 ml). The organic phase was washed with water (10 ml), dried (MgSO4) and evaporated under vacuum, then the residue crystallised from acetone:hexane to give the title compound as an off-white solid (0.35 g, 84%), m.p. 93°-96° C. Found: C,63.39; H,7.73; N,13.39. C11H16N2O2 requires C,63.44; H,7.74; N,13.45%.

Workup

  1. customthis mixture was evaporated under vacuum
  2. customthe residue azeotroped with dimethylformamide (2×20 ml)
  3. customthe solvent was evaporated under vacuum
  4. customthe residue partitioned between water (20 ml) and ethyl acetate (20 ml)
  5. washThe organic phase was washed with water (10 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated under vacuum
  8. customthe residue crystallised from acetone

Sources & evidence

ORD record
ord-b7387c12c23747d48ecedbf2a6c91842
Source dataset
uspto-grants-1997_01
Patent number
US05591742

Reaction notes

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