Pyridine → HCID 22993856, compound

HRID 2116561Notes

Reaction equation

HRID 2116561 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][C:14]2[CH:15]=[C:16]([Cl:20])[CH:17]=[N:18][CH:19]=2)=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].N1C=CC=CC=1.[Cl:27][C:28]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:29]=1[C:30](Cl)=[O:31]>C(Cl)Cl>[Cl:27][C:28]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:29]=1[C:30]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][C:14]2[CH:15]=[C:16]([Cl:20])[CH:17]=[N:18][CH:19]=2)=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:31]

Participants

5

Reactant 3

HCID 1049PyridineHCID 666452,4-Dichlorobenzoyl chlorideHCID 9948021HCID 9948021, compound

Product 1

HCID 22993856HCID 22993856, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the aniline produced in Example 1 (100 mg, 0.34 mmol) in CH2Cl2 (2 mL) was added pyridine (81 μL, 1 mmol) and 2,4-dichlorobenzoyl chloride (140 mg, 0.68 mmol). The mixture was stirred for 90 min. The product was purified by column chromatography on silica gel (gradient elution: 30:1 hexane/ethyl acetate to 7:1 hexane/ethyl acetate) followed by recrystallization from Ch2Cl2/hexanes to yield 126 mg (79%) of the title compound. mp 125-127° C.

Workup

  1. customThe product was purified by column chromatography on silica gel (gradient elution: 30:1 hexane/ethyl acetate to 7:1 hexane/ethyl acetate)
  2. customfollowed by recrystallization from Ch2Cl2/hexanes

Sources & evidence

ORD record
ord-0d191ecb43694bf39ed3b1db45c55b9e
Source dataset
uspto-grants-2008_10
Patent number
US07439242B2

Reaction notes

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