2-Amino-5-chloropyridine → 4-chloro-N-(5-chloropyridin-2-yl)-3-nitrobenzamide

HRID 605212Notes

Reaction equation

HRID 605212 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=2)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 661742-Amino-5-chloropyridineHCID 81531DiisopropylethylamineHCID 1234774-Chloro-3-nitrobenzoyl chloride

Product 1

HCID 6930954-chloro-N-(5-chloropyridin-2-yl)-3-nitrobenzamideYield 42.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloro-3-nitrobenzoyl chloride (1.00 g, 4.99 mmol) in dry methylene chloride (20 mL) under a nitrogen atmosphere was treated with 2-amino-5-chloropyridine (643 mg, 4.99 mmol) and N,N-diisopropylethylamine (1.05 mL, 6.00 mmol), and the resulting mixture stirred at room temperature for 18 hours. The solvent was removed by rotary evaporation in vacuo, the residue taken up in ethyl acetate (100 mL), and washed with saturated aqueous sodium bicarbonate (50 mL), water (2×50 mL), and brine (50 mL). The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Trituration with 5% ethyl acetate/methylene chloride afforded the title compound as a dark yellow solid (660 mg, 42%).

Workup

  1. customThe solvent was removed by rotary evaporation in vacuo
  2. washwashed with saturated aqueous sodium bicarbonate (50 mL), water (2×50 mL), and brine (50 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d9fc8539c0fc4485a34f45d554db6fb9
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

Loading…