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

HRID 1107362Notes

Reaction equation

HRID 1107362 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 crystallized from acetone:hexane to give the title compound as an off-white solid (0.35 g, 84%), m.p. 93-96° C.

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 crystallized from acetone

Sources & evidence

ORD record
ord-1a007527ef3f40c5bb328260f49eec9b
Source dataset
uspto-grants-2000_05
Patent number
US06060477

Reaction notes

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