Triethylamine → Methyl 5-(azidocarbonyl)nicotinate

HRID 732705Notes

Reaction equation

HRID 732705 reaction equation
C1C=CC(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)=CC=1.C1COCC1.CN(C=O)C.[CH3:28][O:29][C:30]([C:32]1[CH:33]=[N:34][CH:35]=[C:36]([CH:40]=1)[C:37]([O-])=[O:38])=[O:31].[K+].C(N(CC)CC)C>C(OCC)(=O)C>[N:15]([C:37]([C:36]1[CH:35]=[N:34][CH:33]=[C:32]([CH:40]=1)[C:30]([O:29][CH3:28])=[O:31])=[O:38])=[N+:16]=[N-:17]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 21974620tetrahydrofuran N,N-dimethylformamideHCID 49760369Potassium 5-(methoxycarbonyl)nicotinate

Product 1

HCID 86628561Methyl 5-(azidocarbonyl)nicotinate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 3.29 ml portion of DPPA was added under ice-cooling to 24 ml of a THF-DMF (1:1) mixed solution of 3.04 g of potassium 5-(methoxycarbonyl)nicotinate and 2.32 ml of triethylamine and stirred at room temperature for 3Hours. The reaction solution was mixed with ethyl acetate, washed with water, saturated sodium bicarbonate aqueous solution and saturated brine in that order and dried with anhydrous magnesium sulfate. By concentrating this under a reduced pressure, methyl 5-(azidocarbonyl)nicotinate was obtained as a pale yellow solid.

Workup

  1. washwashed with water, saturated sodium bicarbonate aqueous solution and saturated brine in that order
  2. dry with materialdried with anhydrous magnesium sulfate
  3. concentrationBy concentrating this under a reduced pressure

Sources & evidence

ORD record
ord-ad0d0660fde04165ab3e0711e260ccb7
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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