1-Naphthol → HCID 86634720, compound

HRID 910923Notes

Reaction equation

HRID 910923 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[C:15]1[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][N:18]=[C:17]([Cl:26])[CH:16]=1>>[Cl:26][C:17]1[CH:16]=[C:15]([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)[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][N:18]=1

Participants

4

Reactant 3

HCID 70051-NaphtholHCID 24758Sodium hydrideHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylate

Product 1

HCID 86634720HCID 86634720, compoundYield 62.4%

Procedure

Using the method of Example 3, Step A, naphthalen-1-ol (2.62 g, 18.2 mmol), 60% sodium hydride in mineral oil (727 mg, 18.2 mmol), and ethyl 4,6-dichloronicotinate (4.00 g, 18.2 mmol) afforded ethyl 6-chloro-4-(naphthalen-1-yloxy)nicotinate (3.72 g, 62% yield) as an oil. 1H NMR (CDCl3) δ 8.86 (s, 1H), 7.94 (d, 2H), 7.82 (d, 1H), 7.49-7.61 (m, 3H), 7.22 (d, 1H), 6.54 (s, 1H), 4.43 (q, 2H), 1.38 (t, 3H).

Sources & evidence

ORD record
ord-ca1d2fa97fd44a15ac8ce7e4529c014e
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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