Ethyl Acetate → 4-(cyclopropylmethoxy)-N-(4,6-dichloropyridin-3-yl)benzamide

HRID 2277178Notes

Reaction equation

HRID 2277178 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[NH2:9].[CH:10]1([CH2:13][O:14][C:15]2[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=2)[CH2:12][CH2:11]1.C(OCC)(=O)C>N1C=CC=CC=1.C1COCC1>[CH:10]1([CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([NH:9][C:3]3[CH:4]=[N:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[O:20])=[CH:22][CH:23]=2)[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 5957294,6-Dichloropyridin-3-amineHCID 867312344-(Cyclopropylmethoxy)benzoyl chloride

Product 1

HCID 867312334-(cyclopropylmethoxy)-N-(4,6-dichloropyridin-3-yl)benzamideYield 36.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,6-dichloropyridin-3-amine (2.00 g) in pyridine (30 mL) was added a solution of 4-(cyclopropylmethoxy)benzoyl chloride (3.88 g) in THF (5 mL), and the mixture was stirred at room temperature for 10 min. The reaction mixture was subjected to silica gel column chromatography (NH, ethyl acetate), and the solvent was evaporated, and the obtained solid was washed with diethyl ether/hexane to give the title compound (1.50 g).

Workup

  1. customthe solvent was evaporated
  2. washthe obtained solid was washed with diethyl ether/hexane

Sources & evidence

ORD record
ord-66fdf7dd845747758c5b14d7fc8c2717
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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