2-Chloro-5-nitropyridine → HCID 86608642, compound

HRID 1455046Notes

Reaction equation

HRID 1455046 reaction equation
[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)[O:17][CH:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:15][CH2:14]3)=[N:8][CH:9]=1)([O-:3])=[O:2].[OH:27]C1C=C(C2CCC3C(=CC=C(O)C=3)O2)C=CC=1.Cl[C:46]1[CH:51]=[CH:50][C:49]([N+:52]([O-:54])=[O:53])=[CH:48][N:47]=1>>[N+:52]([C:49]1[CH:50]=[CH:51][C:46]([O:27][C:25]2[CH:26]=[C:21]([CH:16]3[CH2:15][CH2:14][C:13]4[C:18](=[CH:19][CH:20]=[C:11]([O:10][C:7]5[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=5)[CH:12]=4)[O:17]3)[CH:22]=[CH:23][CH:24]=2)=[N:47][CH:48]=1)([O-:54])=[O:53]

Participants

4

Reactant 3

HCID 783082-Chloro-5-nitropyridineHCID 17978485HCID 17978485, compoundHCID 17978512Orm-10103

Product 1

HCID 86608642HCID 86608642, compound

Procedure

2-[2-(3-(5-Nitropyridin-2-yloxy)phenyl)chroman-6-yloxy]-5-nitropyridine was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1 (b) but starting from 2-(3-hydroxyphenyl)chroman-6-ol and using 210 mol-% of 2-chloro-5-nitropyridine. 1H NMR (400 MHz, d6-DMSO) δ: 9.05 (d, 1H, J 2.9 Hz), 9.03 (d, 1H, J 2.9 Hz), 8.64 (dd, 1H, J 2.9, 9.1 Hz), 8.60 (dd, 1H, J 2.9, 9.1 Hz), 7.52 (t, 1H, J 7.8 Hz), 7.41 (d, 1H, J 7.8 Hz), 7.33-7.31 (m, 1H), 7.28 (d, 1H, J 7.8 Hz), 7.23-7.18 (m, 2H) 7.01-6.90 (m, 3H), 5.20 (dd, 1H, J 2.1, 10.1 Hz), 3.07-2.92 (m, 1H), 2.80-2.70 (m, 1H), 2.30-2.18 (m, 1H), 2.10-1.98 (m, 1H).

Sources & evidence

ORD record
ord-1be723706af04801a47c7e2382d95eb9
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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