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

HRID 911003Notes

Reaction equation

HRID 911003 reaction equation
[CH3:1][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>>[CH3:1][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 157454893-HYDROXY-4-METHYLBENZOIC ACID ETHYL ESTER

Product 1

HCID 86634741Ethyl 4-methyl-3-(2-chloropyridin-4-yloxy)benzoateYield 94%

Procedure

Using the method of Example 3, Step A, ethyl 4-methyl-3-hydroxybenzoate (1.70 g, 9.46 mmol), 60% sodium hydride in mineral oil (378 mg, 9.48 mmol), and 2-chloro-4-nitropyridine (1.50 g, 9.46 mmol) were reacted to provide ethyl 4-methyl-3-(2-chloropyridin-4-yloxy)benzoate (2.59 g, 94% yield) as a clear oil. 1H NMR (CDCl3) δ 8.24 (d, 1H), 7.90 (d, 1H), 7.69 (s, 1H), 7.38 (d, 1H), 6.73 (d, 2H), 4.37 (quartet, 2H), 2.23 (s, 3H), 1.39 (t, 3H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-7cccb841511e43e3a415d09fc1788e00
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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