7-(4-Methoxy-2-nitrophenoxy)-3-phenylchroman → 5-Methoxy-2-(3-phenylchroman-7-yloxy)phenylamine hydrochloride

HRID 31313Notes

Reaction equation

HRID 31313 reaction equation
[ClH:1].COC1C=CC(OC2C=C3C(=CC=2)OC(C2C=CC=CC=2)CC3)=C(N)C=1.[CH3:28][O:29][C:30]1[CH:52]=[CH:51][C:33]([O:34][C:35]2[CH:44]=[C:43]3[C:38]([CH2:39][CH:40]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[CH2:41][O:42]3)=[CH:37][CH:36]=2)=[C:32]([N+:53]([O-])=O)[CH:31]=1>>[ClH:1].[CH3:28][O:29][C:30]1[CH:52]=[CH:51][C:33]([O:34][C:35]2[CH:44]=[C:43]3[C:38]([CH2:39][CH:40]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[CH2:41][O:42]3)=[CH:37][CH:36]=2)=[C:32]([NH2:53])[CH:31]=1

Participants

3

Reactant 2

HCID 179784877-(4-Methoxy-2-nitrophenoxy)-3-phenylchromanHCID 179785505-Methoxy-2-(2-phenylchroman-6-yloxy)phenylamine hydrochloride

Product 1

HCID 179786015-Methoxy-2-(3-phenylchroman-7-yloxy)phenylamine hydrochloride

Procedure

5-Methoxy-2-(3-phenylchroman-7-yloxy)phenylamine hydrochloride was prepared as described for 5-methoxy-2-(2-phenylchroman-6-yloxy)phenylamine hydrochloride in Example 3(b) using 310 mg of 7-(4-methoxy-2-nitrophenoxy)-3-phenylchroman. 1H NMR (400 MHz, d6-DMSO) δ: 7.32-7.35 (m, 4H), 7.23-7.29 (m, 1H), 7.05 (d, 1H, J 8.4 Hz), 6.76 (d, 1H, J 8.8. Hz), 6.46 (d, 1H, J 2.8 Hz), 6.43 (dd, 1H, J 8.4, 2.5 Hz), 6.28 (d, 1H, J 2.5 Hz), 6.24 (dd, 1H, J 8.8, 2.8 Hz), 4.24 (dd, 1H, J 10.4, 3.4 Hz), 4.05 (t, 1H, J 10.4 Hz), 3.18 (m, 1H), 2.88-3.01 (m, 2H).

Sources & evidence

ORD record
ord-8dff93d555c7444e8bd952b545006dea
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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