2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 5-[2-(3-Chloro-phenyl)-ethoxy]-4-ethyl-nicotinic acid ethyl ester

HRID 1475764Notes

Reaction equation

HRID 1475764 reaction equation
C1(OC([N:10]2[CH:15]=[C:14]([O:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[CH:13]([CH2:26][CH3:27])[C:12]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:11]2)=O)C=CC=CC=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl>[CH2:31]([O:30][C:28](=[O:29])[C:12]1[C:13]([CH2:26][CH3:27])=[C:14]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH:15]=[N:10][CH:11]=1)[CH3:32]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 671712595-[2-(3-Chloro-phenyl)-ethoxy]-4-ethyl-4H-pyridine-1,3-dicarboxylic acid 3-ethyl ester 1-phenyl ester

Product 1

HCID 671712745-[2-(3-Chloro-phenyl)-ethoxy]-4-ethyl-nicotinic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound of step 2 (80 mg, 0.175 mmol)) was dissolved in dichloromethane. 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (80 mg, 0.35 mmol) was added and the mixture was stirred over night at room temperature. The mixture was partitioned between ethyl acetate and saturated sodium hydrogencarbonate solution with addition of some sodium sulfit. The combined organic extracts were dried over sodium chloride and evaporated to dryness in vacuo. The material was titured with diethyl ether, the solid material was separated by suction filtration, the filtrate was evaporated to dryness, again, to yield the title compound.

Workup

  1. customThe mixture was partitioned between ethyl acetate and saturated sodium hydrogencarbonate solution with addition of some sodium sulfit
  2. dry with materialThe combined organic extracts were dried over sodium chloride
  3. customevaporated to dryness in vacuo
  4. customthe solid material was separated by suction filtration
  5. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-6f553f3e4bbc42bea8cc27659552ae81
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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