2-Chloro-5-nitropyridine → HCID 86608639, compound

HRID 1455047Notes

Reaction equation

HRID 1455047 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7](OC2C=C3C(=CC=2)OC(C2C=CC=CC=2)CC3)=[N:8][CH:9]=1)([O-:3])=[O:2].[OH:27][C:28]1[CH:29]=[C:30]([CH:34]2[CH2:43][CH:42]([OH:44])[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([OH:45])[CH:40]=3)[O:35]2)[CH:31]=[CH:32][CH:33]=1.Cl[C:47]1[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][N:48]=1>>[N+:53]([C:50]1[CH:51]=[CH:52][C:47]([O:45][C:39]2[CH:40]=[C:41]3[C:36](=[CH:37][CH:38]=2)[O:35][CH:34]([C:30]2[CH:31]=[CH:32][CH:33]=[C:28]([O:27][C:7]4[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=4)[CH:29]=2)[CH2:43][CH:42]3[OH:44])=[N:48][CH:49]=1)([O-:55])=[O:54]

Participants

4

Reactant 3

HCID 783082-Chloro-5-nitropyridineHCID 17978512Orm-10103HCID 179785322-(3-Hydroxyphenyl)chroman-4,6-diol

Product 1

HCID 86608639HCID 86608639, compound

Procedure

6-(5-Nitropyridin-2-yloxy)-2-[3-(5-nitropyridin-2-yloxy)phenyl]chroman-4-ol was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1 (b) but starting from 2-(3-hydroxyphenyl)chroman-4,6-diol and using 210 mol-% of 2-chloro-5-nitropyridine. 1H NMR (400 MHz, d6-DMSO) δ: 9.06 (d, 1H, J 2.8 Hz), 9.03 (d, 1H, J 2.8 Hz), 8.64 (dd, 1H, J 2.8, 9.1 Hz), 8.61 (dd, 1H, J 2.8, 9.1 Hz), 7.54 (t, 1H, J 7.9 Hz), 7.43 (d, 1H, J 7.9 Hz), 7.36 (s, 1H), 7.30 (d, 1H, J 9.1 Hz), 7.25-7.21 (m, 3H) 7.01 (dd, 1H, J 2.9, 8.7 Hz), 6.89 (d, 1H, J 8.7 Hz), 5.67 (d, 1H, J 6.4 Hz), 5.36 (d, 1H, J 10.8 Hz), 5.01-4.95 (m, 1H), 2.41-2.36 (m, 1H), 2.02-1.92 (m, 1H).

Sources & evidence

ORD record
ord-89474066dae04e34b2ce1606c4574159
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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