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

HRID 31324Notes

Reaction equation

HRID 31324 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=CC=1C1CCC2C(=CC=C(O)C=2)O1)([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][CH:24]=[CH:25][C:26]=2[N+:27]([O-:29])=[O:28])[CH2:15][CH2:14]3)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 17978512Orm-10103HCID 179785132-(2-Nitrophenyl)chroman-6-ol

Product 1

HCID 179785625-Nitro-2-[2-(2-nitrophenyl)chroman-6-yloxy]pyridine

Procedure

5-Nitro-2-[2-(2-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-(2-nitrophenyl)chroman-6-ol. 1H NMR (400 MHz, d6-DMSO) δ: 9.04 (d, 1H, J 2.9 Hz), 8.60 (dd, 1H, J 9.1, 2.9 Hz), 8.03 (d, 1H, J 7.9 Hz), 7.80-7.85 (m, 2H), 7.62-7.66 (m, 1H), 7.22 (d, 1H, J 9.1 Hz), 7.04 (d, 1H, J 2.8 Hz), 6.98 (dd, 1H, J 8.8, 2.8 Hz), 6.88 (d, 1H, J 8.8 Hz), 5.52 (dd, 1H, J 10.3, 2.0 Hz), 2.99-3.31 (m, 1H), 2.80-2.85 (m, 1H), 2.35-2.40 (m, 1H), 1.99-2.04 (m, 1H).

Sources & evidence

ORD record
ord-8ee9d56efaa4445596cf453fa58f145a
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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