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

HRID 911004Notes

Reaction equation

HRID 911004 reaction equation
[CH3:1][C:2]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[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[C:12]([O:13][C:21]2[CH:20]=[CH:19][N:18]=[C:17]([Cl:16])[CH:22]=2)=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 7351522-Chloro-4-nitropyridineHCID 15376194Ethyl 3-hydroxy-2-methylbenzoate

Product 1

HCID 86634742Ethyl 2-methyl-3-(2-chloropyridin-4-yloxy)benzoateYield 90%

Procedure

Using the method of Example 3, Step A, ethyl 2-methyl-3-hydroxybenzoate (2.27 g, 12.6 mmol), 60% sodium hydride in mineral oil (505 mg, 12.6 mmol), and 2-chloro-4-nitropyridine (2.00 g, 12.6 mmol) were reacted to provide ethyl 2-methyl-3-(2-chloropyridin-4-yloxy)benzoate (3.31 g, 90% yield) as a clear oil. 1H NMR (CDCl3) δ 8.22 (d, 1H), 7.83 (d, 1H), 7.33 (t, 1H), 7.18 (d, 1H), 6.70-6.72 (m, 2H), 4.39 (quartet, 2H), 2.38 (s, 3H), 1.41 (t, 3H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-4085ddfd86184cada133736df7f11989
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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