Methyl Salicylate → HCID 86634716, compound

HRID 910905Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[Cl:14][C:15]1[CH:20]=[C:19]([N+]([O-])=O)[CH:18]=[CH:17][N:16]=1>>[Cl:14][C:15]1[CH:20]=[C:19]([O:1][C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])[CH:18]=[CH:17][N:16]=1

Participants

Reactant 3

HCID 4133Methyl Salicylate

HCID 24758Sodium hydride

HCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 86634716HCID 86634716, compoundYield 70.4%

Procedure

Using the method of Example 3, Step A, methyl 2-hydroxybenzoate (2.88 mg, 18.9 mmol), 60% sodium hydride in mineral oil (757 mg, 18.9 mmol), and 2-chloro-4-nitropyridine (3.00 g, 18.9 mmol) were reacted to provide methyl 2-(2-chloropyridin-4-yloxy)benzoate (3.51 g, 70% yield) as an oil. 1H NMR (CDCl3) δ 8.22 (d, 1H), 8.05 (d, 1H), 7.63 (t, 1H), 7.40 (t, 1H), 7.16 (d, 1H), 6.72-6.74 (m, 1H), 3.77 (s, 1H).

Workup

customwere reacted

Sources & evidence

ORD record: ord-ff968faab45f4967b4ae23d759587c57
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022222B2

Reaction notes

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