1-Naphthol → HCID 18520070, compound

HRID 910903Notes

Reaction equation

HRID 910903 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[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:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[CH:18]=[CH:17][N:16]=1

Participants

4

Reactant 3

HCID 70051-NaphtholHCID 24758Sodium hydrideHCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 18520070HCID 18520070, compoundYield 95%

Procedure

Using the method of Example 3, Step A, naphthalen-1-ol (909 mg, 6.31 mmol), 60% sodium hydride in mineral oil (252 mg, 6.31 mmol), and 2-chloro-4-nitropyridine (1.00 g, 6.31 mmol) afforded 2-chloro-4-(naphthalen-1-yloxy)pyridine (1.53 g, 95% yield) as an oil. 1H NMR (CDCl3) δ 8.22 (d, 1H), 7.93 (d, 1H), 7.86 (d, 1H), 7.81 (d, 1H), 7.48-7.56 (m, 3H), 7.21 (d, 1H), 6.79-6.83 (m, 2H).

Sources & evidence

ORD record
ord-a82984ec743345109313f669d885b3e6
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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