7-Hydroxyflavanone → 7-(5-Nitropyridin-2-yloxy)-2-phenylchroman-4-one

HRID 31171Notes

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

Participants

Reactant 2

HCID 18907-Hydroxyflavanone

HCID 17978512Orm-10103

Product 1

HCID 179786057-(5-Nitropyridin-2-yloxy)-2-phenylchroman-4-one

Procedure

7-(5-Nitropyridin-2-yloxy)-2-phenylchroman-4-one was prepared as described for 5-Nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) using 150 mg of 7-hydroxyflavanone. 1H NMR (400 MHz, d6-DMSO) δ: 9.07 (d, 1H, J 2.8 Hz), 8.67 (dd, 1H, J 9.0, 2.8 Hz), 7.89 (d, 1H, 8.6 Hz), 7.60-7.35 (m, 6H), 7.04 (d, 1H, 2.1 Hz), 6.97 (dd, 1 H, 8.6, 2.1 HZ), 5.75 (dd, 1H, J 13.0, 2.7 Hz), 3.32 (dd, 1H, 16.9, 13.0 Hz), 2.85 (d, −16.9, 2.7 Hz).

Sources & evidence

ORD record: ord-c7e33133580146e6959330860266a988
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425568B2

Reaction notes

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