Nicotinic Acid → 2-Acetyl-6-nitrophenyl nicotinate

HRID 876523Notes

Reaction equation

HRID 876523 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12].[C:14](O)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:14]([O:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=1

Participants

6

Reactant 3

HCID 938Nicotinic AcidHCID 10868DicyclohexylcarbodiimideHCID 2700261-(2-Hydroxy-3-nitrophenyl)-ethanone

Product 1

HCID 584773042-Acetyl-6-nitrophenyl nicotinateYield 82.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(2-Hydroxy-3-nitrophenyl)ethanone 1 (1.0 g, 5.5 mmol), nicotinic acid 4 (0.8 g, 5.8 mmol), DCC (2.4 g, 11.6 mmol) and DMAP (0.7 g, 5.8 mmol) in CH2Cl2 (30 mL) was stirred at room temperature for 12 hours. After cooling to 0° C., the precipitated dicyclohexyl urea was removed by filtration and the filtrate concentrated. The crude residue was purified by flash chromatography eluting with Pentane/EtOAc (10:1) to give 5 (1.3 g, 81% yield).

Workup

  1. temperatureAfter cooling to 0° C.
  2. customthe precipitated dicyclohexyl urea was removed by filtration
  3. concentrationthe filtrate concentrated
  4. customThe crude residue was purified by flash chromatography
  5. washeluting with Pentane/EtOAc (10:1)

Sources & evidence

ORD record
ord-a4d1fb0c215e43fd96fda7583c0369bd
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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