Pyridine → HCID 16731657, compound

HRID 1883044Notes

Reaction equation

HRID 1883044 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:12]([O-:14])=[O:13])=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.C(Cl)(=O)C(Cl)=O.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=1.N1C=CC=CC=1>ClCCl.CN(C)C=O.O>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[C:4]=2[N+:12]([O-:14])=[O:13])=[N:23][CH:24]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 661742-Amino-5-chloropyridineHCID 786323-Methoxy-2-nitrobenzoic acid

Product 1

HCID 16731657HCID 16731657, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirring suspension of 3-methoxy-2-nitrobenzoic acid (14.5 g, 73.5 mmol) in dichloromethane (100 mL) was added a couple of drops of N,N-dimethylformamide followed by oxalyl chloride (6.7 mL, 77.1 mmol). The reaction was stirred at room temperature overnight and the residue transferred slowly to an ice cold solution of 2-amino-5-chloropyridine (9 g, 70 mmol) and pyridine (20 mL) in dichloromethane (200 mL). The reaction was stirred overnight, treated with water, and concentrated. The resulting mixture was treated with ethyl acetate, washed consecutively with aqueous citric acid, saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by recrystallization from toluene to give 17 g (79%) of a white solid.

Workup

  1. stirringThe reaction was stirred overnight
  2. concentrationconcentrated
  3. additionThe resulting mixture was treated with ethyl acetate
  4. washwashed consecutively with aqueous citric acid, saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by recrystallization from toluene

Sources & evidence

ORD record
ord-c6d29a0433fa49ed9e271fdac639426c
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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