Triethylamine → 6-Chloro-nicotinic acid 3-methoxycarbonyl-1-methyl-2-oxo-propyl ester

HRID 854579Notes

Reaction equation

HRID 854579 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH3:11][O:12][C:13](=[O:20])[CH2:14][C:15](=[O:19])[CH:16](Br)[CH3:17].C(N(CC)CC)C>CC(C)=O>[CH3:11][O:12][C:13]([CH2:14][C:15](=[O:19])[CH:16]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[N:3][CH:4]=1)[CH3:17])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 792226-Chloronicotinic acidHCID 9815681Methyl 4-bromo-3-oxopentanoate

Product 1

HCID 866045856-Chloro-nicotinic acid 3-methoxycarbonyl-1-methyl-2-oxo-propyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 6-Chloro-nicotinic acid (10 g, 63.5 mmol) and 4-Bromo-3-oxo-pentanoic acid methyl ester (1.51 g, 7.2 mmol) (14.6 g, 70 mmol) in acetone (100 mL) is added triethyl amine (9.76 mL, 70 mmol) at 0-5° C. After addition, the reaction mixture is warmed to room temperature and stirred overnight, solid is filtered off, the filtrate is concentrated and taken into methylene chloride, washed with water and brine, dried. The residue is purified by column giving 6-chloro-nicotinic acid 3-methoxycarbonyl-1-methyl-2-oxo-propyl ester (16.3 g.

Workup

  1. additionAfter addition
  2. filtrationsolid is filtered off
  3. concentrationthe filtrate is concentrated
  4. washwashed with water and brine
  5. customdried
  6. customThe residue is purified by column

Sources & evidence

ORD record
ord-64245b41df614cfcb7a0df9f7c762d3c
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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