Phosphorus oxychloride → 2-Chloro-6-(2,6-diethyl-phenyl)-4-ethyl-nicotinic acid methyl ester

HRID 251599Notes

Reaction equation

HRID 251599 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[C:9]([CH2:10][CH3:11])=[CH:8][C:7]([C:12]2[C:17]([CH2:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:20][CH3:21])=[N+:6]([O-])[CH:5]=1.O=P(Cl)(Cl)[Cl:26]>>[CH3:1][O:2][C:3](=[O:23])[C:4]1[C:9]([CH2:10][CH3:11])=[CH:8][C:7]([C:12]2[C:17]([CH2:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:20][CH3:21])=[N:6][C:5]=1[Cl:26]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 669936046-(2,6-diethyl-phenyl)-4-ethyl-nicotinic acid methyl ester N-oxide

Product 1

HCID 596782342-Chloro-6-(2,6-diethyl-phenyl)-4-ethyl-nicotinic acid methyl ester

Conditions

Temperature
80 °C

Procedure

A mixture of 6-(2,6-diethyl-phenyl)-4-ethyl-nicotinic acid methyl ester N-oxide (1.7 g) and POCl3 (10 mL) is heated at 80° C. for 2 hours. The volatile material is removed in vacuo. Ice water and ether is added to the residue. The organic layer is separated and the aqueous layer is extracted with ether. The combined extract is washed with brine, dried, and concentrated to give 2-chloro-6-(2,6-diethyl-phenyl)-4-ethyl-nicotinic acid methyl ester. 1H NMR (CDCl3) 7.26 (t, 1H), 7.12 (d, 3H), 4.02 (s, 3H), 2.69 (q, 2H), 2.32 (m, 4H), 1.25 (t, 3H), 1.07 (t, 6H).

Workup

  1. customThe volatile material is removed in vacuo
  2. additionIce water and ether is added to the residue
  3. customThe organic layer is separated
  4. extractionthe aqueous layer is extracted with ether
  5. extractionThe combined extract
  6. washis washed with brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-379cfba3c679470388baef0e9244a380
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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