5-Methoxy-2-(2-phenylchroman-6-yloxy)phenylamine hydrochloride → 2-[2-(2,5-Difluorophenyl)chroman-6-yloxy]-5-ethoxyphenylamine Hydrochloride

HRID 31268Notes

Reaction equation

HRID 31268 reaction equation
[ClH:1].COC1C=CC(OC2C=C3C(=CC=2)OC(C2C=CC=CC=2)CC3)=C(N)C=1.[F:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=1[CH:36]1[CH2:45][CH2:44][C:43]2[C:38](=[CH:39][CH:40]=[C:41]([O:46][C:47]3[CH:52]=[CH:51][C:50]([O:53][CH2:54][CH3:55])=[CH:49][C:48]=3[N+:56]([O-])=O)[CH:42]=2)[O:37]1>>[ClH:1].[F:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=1[CH:36]1[CH2:45][CH2:44][C:43]2[C:38](=[CH:39][CH:40]=[C:41]([O:46][C:47]3[CH:52]=[CH:51][C:50]([O:53][CH2:54][CH3:55])=[CH:49][C:48]=3[NH2:56])[CH:42]=2)[O:37]1

Participants

3

Reactant 2

HCID 179785505-Methoxy-2-(2-phenylchroman-6-yloxy)phenylamine hydrochlorideHCID 179785682-(2,5-Difluorophenyl)-6-(4-ethoxy-2-nitrophenoxy)chroman

Product 1

HCID 179786142-[2-(2,5-Difluorophenyl)chroman-6-yloxy]-5-ethoxyphenylamine Hydrochloride

Procedure

2-[2-(2,5-Difluorophenyl)chroman-6-yloxy]-5-ethoxyphenylamine hydrochloride was prepared as described for 5-methoxy-2-(2-phenylchroman-6-yloxy)phenylamine hydrochloride in example 3(b) starting from 120 mg of 2-(2,5-difluorophenyl)-6-(4-ethoxy-2-nitrophenoxy)chroman. 1H NMR (400 MHz, CDCl3) δ: 7.26-7.22 (m, 2H), 7.01-6.74 (m, 7H), 5.22 (d, 1H, J 9.1 Hz), 3.90 (q, 2H, J 6.9 Hz), 2.90 (m, 1H), 2.68 (m, 1H), 2.19 (m, 1H), 1.90 (m, 1H), 1.34 (t, 3H, 6.9 Hz).

Sources & evidence

ORD record
ord-0876f7da787e4831afca9e1b52a10102
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

Loading…