Water → N-ethyl 5-nitro-2-(3-chloro-5-pyridyloxy)benzamide

HRID 1167659Notes

Reaction equation

HRID 1167659 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([OH:14])[CH:13]=1.[CH2:15]([NH:17][C:18](=[O:29])[C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1Cl)[CH3:16].O>C1COCC1.CCOCC>[CH2:15]([NH:17][C:18](=[O:29])[C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1[O:14][C:12]1[CH:13]=[C:8]([Cl:7])[CH:9]=[N:10][CH:11]=1)[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 5823053-Hydroxy-5-chloropyridineHCID 4380195N-ethyl-2-chloro-5-nitrobenzamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 12109362N-ethyl 5-nitro-2-(3-chloro-5-pyridyloxy)benzamideYield 52%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a suspension of potassium t-butoxide (1.5 g) in THF (15 mL) was added 3-chloro-5-hydroxypyridine (1.79 g, mmol). To this solution was added a solution of N-ethyl-2-chloro-5-nitrobenzamide (2.76 g, mmol) in THF (15 mL). The resulting mixture was heated at 50° C. for 84 hr. After cooling, the reaction mixture was diluted into a mixture of water and ether. Solids were collected by filtration, washed with water then with ether, and dried under vacuum to afford N-ethyl 5-nitro-2-(3-chloro-5-pyridyloxy)benzamide (2.0 g, 52%). mp 165-167° C.

Workup

  1. temperatureAfter cooling
  2. filtrationSolids were collected by filtration
  3. washwashed with water
  4. dry with materialwith ether, and dried under vacuum

Sources & evidence

ORD record
ord-4715592c80bd4f74bb9f4064492a8ab2
Source dataset
uspto-grants-2003_09
Patent number
US06620827B2

Reaction notes

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