2-(2-Phenylchroman-6-yloxy)-aniline → 3-Amino-5-(trifluoromethyl)-2-(2-phenylchroman-6-yloxy)-aniline

HRID 31236Notes

Reaction equation

HRID 31236 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([N+:14]([O-])=O)[C:5]=1[O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[O:24][CH:23]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:22][CH2:21]2)([O-])=O.C1(C2CCC3C(=CC=C(OC4C=CC=CC=4N)C=3)O2)C=CC=CC=1>[Zn].C(O)(=O)C>[NH2:14][C:6]1[C:5]([O:17][C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[O:24][CH:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:22][CH2:21]3)=[C:4]([CH:9]=[C:8]([C:10]([F:12])([F:13])[F:11])[CH:7]=1)[NH2:1]

Participants

5

Reactant 2

HCID 179785582-(2-Phenylchroman-6-yloxy)-anilineHCID 179785802,6-Dinitro-1-(2-phenylchroman-6-yloxy)-4-trifluoromethylbenzene

Product 1

HCID 179784793-Amino-5-(trifluoromethyl)-2-(2-phenylchroman-6-yloxy)-aniline

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

2,6-Dinitro-1-(2-phenylchroman-6-yloxy)-4-trifluoromethylbenzene (0.198 g; 0.43 mmol) was reduced to corresponding diamino compound as described for 2-(2-phenylchroman-6-yloxy)-aniline in Example 29 except that 25 ml of glacial acetic acid and 1.525 g of metallic zinc powder were used. Product was purified by column chromatography (100% CH2Cl2 as the eluant). 1H-NMR (400 MHz; d6-DMSO): δ 7.45-7.28 (m, 5H), 6.76 (d, 1H, J=8.8 Hz), 6.65 (dd, 1H, J=8.7 Hz, J=3.0 Hz), 6.62 (d, 1H, J=2.8 Hz), 5.04 (dd, 1H, J=10.0 Hz, J=2.1 Hz), 4.98 (s, 4H), 2.98-2.86 (m, 1H), 2.70-2.60 (m, 1H), 2.18-2.09 (m, 1H), 2.00-1.88 (m, 1H).

Workup

  1. customProduct was purified by column chromatography (100% CH2Cl2 as the eluant)

Sources & evidence

ORD record
ord-48f35ca2cb2f49f88ab1d45519fa5fdc
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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