Nicotinic Acid → 3-Pyridinecarbonyl Azide

HRID 1281171Notes

Reaction equation

HRID 1281171 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C(N(CC)CC)C.C1(P([N:31]=[N+:32]=[N-:33])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C)C=O>[C:1]([N:31]=[N+:32]=[N-:33])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 199143-Pyridinecarbonyl Azide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

There are added to a suspension of 12.3 g of nicotinic acid in 100 ml of dimethylformamide 14.2 ml of triethylamine and then, after cooling to 0° C., 22 ml of diphenylphosphoryl azide in 50 ml of dimethylformamide. After stirring for 2 hours, the reaction mixture is poured onto ice. After extraction with ether, the organic phase is washed with a NaHCO3 solution, dried, and then concentrated to yield 9.68 g of the expected product.

Workup

  1. additionthe reaction mixture is poured onto ice
  2. extractionAfter extraction with ether
  3. washthe organic phase is washed with a NaHCO3 solution
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9a525fbd895f40dc8dbd8d21d05b3f78
Source dataset
uspto-grants-2002_09
Patent number
US06452015B2

Reaction notes

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