2-(4-Methoxyphenyl)chroman-4,6-diol → 2-(4-Methoxyphenyl)-6-(5-nitropyridin-2-yloxy)chroman-4-ol

HRID 31331Notes

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].[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]2[CH2:44][CH:43]([OH:45])[C:42]3[C:37](=[CH:38][CH:39]=[C:40]([OH:46])[CH:41]=3)[O:36]2)=[CH:31][CH:30]=1>>[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]2[CH2:44][CH:43]([OH:45])[C:42]3[C:37](=[CH:38][CH:39]=[C:40]([O:46][C:7]4[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=4)[CH:41]=3)[O:36]2)=[CH:31][CH:30]=1

Participants

Reactant 2

HCID 179784492-(4-Methoxyphenyl)chroman-4,6-diol

HCID 17978512Orm-10103

Product 1

HCID 179786092-(4-Methoxyphenyl)-6-(5-nitropyridin-2-yloxy)chroman-4-ol

Procedure

2-(4-Methoxyphenyl)-6-(5-nitropyridin-2-yloxy)chroman-4-ol was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) starting from 2-(4-methoxyphenyl)chroman-4,6-diol. 1H NMR (400 MHz, d6-DMSO) δ: 9.04 (d, 1H, J 2.9 Hz), 8.61 (dd, 1H, J 9.1, 2.9 Hz), 7.40 (d, 2H, J 8.7 Hz), 7.24 (d, 1H, J 2.8 Hz), 7.22 (d, 1H, J 9.1 Hz), 7.00 (dd, 1H, J 8.7, 2.8 Hz), 6.97 (d, 2H, J 8.7 Hz), 6.84 (d, 1H, J 8.7 Hz), 5.63 (d, 1H, J 6.4 Hz), 5.23 (d, 1H, J 10.8 Hz), 4.95-5.02 (m, 1H), 3.78 (s, 3H), 2.25-2.29 (m, 1H), 1.98-2.04 (m, 1H).

Sources & evidence

ORD record: ord-0dad45f8c0754a5490a180499e3982da
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425568B2

Reaction notes

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