3-Amino-5-(trifluoromethyl)-2-(2-phenylchroman-6-yloxy)-aniline → 2-(2-Phenylindan-5-yloxy)-5-trifluoromethylbenzene-1,3-diamine

HRID 31247Notes

Reaction equation

HRID 31247 reaction equation
C1(C2CCC3C(=CC=C(OC4C(N)=CC(C(F)(F)F)=CC=4N)C=3)O2)C=CC=CC=1.[N+:30]([C:33]1[CH:54]=[C:53]([C:55]([F:58])([F:57])[F:56])[CH:52]=[C:51]([N+:59]([O-])=O)[C:34]=1[O:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[CH2:41][CH:40]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:39]2)([O-])=O>>[C:45]1([CH:40]2[CH2:39][C:38]3[C:42](=[CH:43][CH:44]=[C:36]([O:35][C:34]4[C:51]([NH2:59])=[CH:52][C:53]([C:55]([F:57])([F:58])[F:56])=[CH:54][C:33]=4[NH2:30])[CH:37]=3)[CH2:41]2)[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

3

Reactant 2

HCID 179784793-Amino-5-(trifluoromethyl)-2-(2-phenylchroman-6-yloxy)-anilineHCID 179785235-(2,6-Dinitro-4-trifluoromethylphenoxy)-2-phenylindan

Product 1

HCID 179785062-(2-Phenylindan-5-yloxy)-5-trifluoromethylbenzene-1,3-diamine

Procedure

2-(2-Phenylindan-5-yloxy)-5-trifluoromethylbenzene-1,3-diamine was prepared as described for 2-(2-phenylchroman-6-yloxy)-5-trifluoromethylbenzene-1,3-diamine in Example 35(b) using 230 mg of 5-(2,6-dinitro-4-trifluoromethylphenoxy)-2-phenylindan. 1H-NMR (300 MHz, d6-DMSO): 7.33-7.27 (m, 4H), 7.22-7.18 (m, 1H), 7.14 (d, 1H, J 8.1 Hz), 6.73-6.69 (m, 2H), 6.31 (s, 2H), 4.98 (s, 4H), 3.64 (k, 1H, J 8.5 Hz), 3.26-3.18 (m, 2H), 2.96-2.86 (m, 2H).

Sources & evidence

ORD record
ord-b682c2f264c24d7eaf0c8d305c8529ae
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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