5-(4-Methoxy-2-nitrophenoxy)-2-phenylindane → 5-Methoxy-2-(2-phenylindan-5-yloxy)phenylamine

HRID 31243Notes

Reaction equation

HRID 31243 reaction equation
COC1C=CC(OC2C=C3C(=CC=2)OC(C2C=CC=CC=2)CC3)=C(N)C=1.[CH3:27][O:28][C:29]1[CH:50]=[CH:49][C:32]([O:33][C:34]2[CH:35]=[C:36]3[C:40](=[CH:41][CH:42]=2)[CH2:39][CH:38]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:37]3)=[C:31]([N+:51]([O-])=O)[CH:30]=1>>[CH3:27][O:28][C:29]1[CH:50]=[CH:49][C:32]([O:33][C:34]2[CH:35]=[C:36]3[C:40](=[CH:41][CH:42]=2)[CH2:39][CH:38]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:37]3)=[C:31]([NH2:51])[CH:30]=1

Participants

3

Reactant 2

HCID 179784835-(4-Methoxy-2-nitrophenoxy)-2-phenylindaneHCID 179784925-Methoxy-2-(2-phenylchroman-6-yloxy)phenylamine

Product 1

HCID 179786425-Methoxy-2-(2-phenylindan-5-yloxy)phenylamine

Procedure

5-Methoxy-2-(2-phenylindan-5-yloxy)phenylamine was prepared as described for 5-methoxy-2-(2-phenylchroman-6-yloxy)phenylamine in Example 3(b) using 200 mg of 5-(4-methoxy-2-nitrophenoxy)-2-phenylindane. 1H-NMR (400 MHz, d6-DMSO): 7.33-7.27 (m, 4H), 7.23-7.18 (m, 2H), 6.82 (d, 1H, J 8.4 Hz), 6.81 (s, 1H), 6.77 (dd, 1H, J 2.3, 8.4 Hz), 6.69 (d, 1H, J 2.3 Hz), 6.48 (bd, 1H, J 6.4 Hz), 3.71 (s, 3H), 3.66 (k, 1H, J 8.3 Hz), 3.24 (dd, 2H, J 8.3, 15.6 Hz), 2.93 (m, 2H). (M)+=331 (100%)

Sources & evidence

ORD record
ord-19787c3dd693457ead1d1158d389fc01
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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