Orm-10103 → 5-Nitro-2-[2-(4-nitrophenyl)chroman-6-yloxy]pyridine

HRID 31320Notes

Reaction equation

HRID 31320 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].[N+:27](C1C=CC(C2CCC3C(=CC=C(O)C=3)O2)=CC=1)([O-:29])=[O:28]>>[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:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)[CH2:15][CH2:14]3)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 17978512Orm-10103HCID 17978633HCID 17978633, compound

Product 1

HCID 179784845-Nitro-2-[2-(4-nitrophenyl)chroman-6-yloxy]pyridine

Procedure

5-Nitro-2-[2-(4-nitrophenyl)chroman-6-yloxy]pyridine was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) starting from 2-(4-nitrophenyl)chroman-6-ol. 1H NMR (300 MHz, d6-DMSO) δ: 9.04 (d, 1H, J 2.9 Hz), 8.60 (dd, 1H, J 9.1, 2.9 Hz), 8.29 (d, 2H, J 6.9 Hz), 7.76 (d, 2H, J 6.9 Hz), 7.21 (d, 1H, J 9.1 Hz), 6.98-7.02 (m, 3H), 5.35 (dd, 1H, J 9.9, 2.2 Hz), 2.96-3.05 (m, 1H), 2.73-2.78 (m, 1H), 2.24-2.29 (m, 1H), 1.96-2.04 (m, 1H).

Sources & evidence

ORD record
ord-e8836e77701942c4831b16685927c681
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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