Sodium hydride → Ethyl 4-chloro-3-(2-chloropyridin-4-yloxy)benzoate

HRID 910994Notes

Reaction equation

HRID 910994 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[OH:13].[H-].[Na+].[Cl:16][C:17]1[CH:22]=[C:21]([N+]([O-])=O)[CH:20]=[CH:19][N:18]=1>>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][C:21]1[CH:20]=[CH:19][N:18]=[C:17]([Cl:16])[CH:22]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 7351522-Chloro-4-nitropyridineHCID 58847555Ethyl 4-chloro-3-hydroxybenzoate

Product 1

HCID 86634737Ethyl 4-chloro-3-(2-chloropyridin-4-yloxy)benzoateYield 76.6%

Procedure

Using the method of Example 3, Step A, ethyl 4-chloro-3-hydroxybenzoate (0.759 g, 3.78 mmol), 60% sodium hydride in mineral oil (151 mg, 3.78 mmol), and 2-chloro-4-nitropyridine (0.600 g, 3.78 mmol) were reacted to provide ethyl 4-chloro-3-(2-chloropyridin-4-yloxy)benzoate (0.904 g, 76% yield) as a white solid. 1H NMR (CDCl3) δ 8.27 (d, 1H), 7.96 (d, 1H), 7.84 (s, 1H), 7.60 (d, 1H), 6.77 (s, 1H), 6.76 (d, 1H), 4.39 (quartet, 2H), 1.41 (t, 2H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-05c08dd2d35144418606a6adbaeba2d9
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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