2-Chloro-5-nitropyridine → HCID 17978639, compound

HRID 31224Notes

Reaction equation

HRID 31224 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:20]=[CH:19][C:18]3[CH2:17][CH:16]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:15][CH2:14][C:13]=3[CH:12]=2)=[N:8][CH:9]=1)([O-:3])=[O:2].[OH:27]C1C=C2C(=CC=1)C(=O)C(C1C=CC=CC=1)CC2.ClC1C=CC([N+]([O-])=O)=CN=1.[F-].[K+]>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17](=[O:27])[CH:16]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:15][CH2:14]3)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 783082-Chloro-5-nitropyridineHCID 522689Potassium FluorideHCID 17978530HCID 17978530, compoundHCID 179785426-hydroxy-2-phenyl-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 17978639HCID 17978639, compound

Procedure

6-(5-Nitro-pyridin-2-yloxy)-2-phenyl-3,4-dihydro-2H-naphthalen-1-one was prepared as described for 5-nitro-2-(6-phenyl-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-pyridine in Example 23(d) using 50 mg 6-hydroxy-2-phenyl-3,4-dihydro-2H-naphthalen-1-one, 33 mg 2-chloro-5-nitropyridine and 37 mg potassium fluoride. 1H NMR (400 MHz, d6-DMSO) δ: 9.07 (d, 1H, J 2.8 Hz), 8.68 (dd, 1H, J 9.0, 2.9), 8.01 (d, 1H, J 8.5), 7.37 (d, 1H, J 9.1 Hz), 7.21-7.38 (m, 7H), 3.96-4.04 (m, 1H), 3.15-3.23 (m, 1H), 2.98-3.04 (m, 1H), 2.39-2.48 (m, 1H), 2.25-2.31 (m, 1H).

Sources & evidence

ORD record
ord-31336667031a456ab69adc4f491c97bc
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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