2-(2-Phenylchroman-6-yloxy)-aniline → 5-Trifluoromethyl-2-(2-phenylchroman-6-yloxy)-aniline

HRID 31228Notes

Reaction equation

HRID 31228 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[O:21][CH:20]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:19][CH2:18]2)([O-])=O.C1(C2CCC3C(=CC=C(OC4C=CC=CC=4N)C=3)O2)C=CC=CC=1>C(O)(=O)C.[Zn]>[F:13][C:10]([F:11])([F:12])[C:8]1[CH:7]=[CH:6][C:5]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[O:21][CH:20]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:19][CH2:18]3)=[C:4]([CH:9]=1)[NH2:1]

Participants

5

Reactant 2

HCID 179785582-(2-Phenylchroman-6-yloxy)-anilineHCID 179786542-Nitro-1-(2-phenylchroman-6-yloxy)-4-trifluoromethylbenzene

Product 1

HCID 179785005-Trifluoromethyl-2-(2-phenylchroman-6-yloxy)-aniline

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

2-Nitro-1-(2-phenylchroman-6-yloxy)-4-trifluoromethylbenzene (0.311 g) was reduced in 25 ml of glacial acetic acid with zinc (1.48 g) as described for 2-(2-phenylchroman-6-yloxy)-aniline in Example 29. Product was purified by column chromatography (CH2Cl2:n-heptane/70:30 as the eluant). 1H-NMR (300 MHz; d6-DMSO): δ 7.48-7.28 (m, 5H), 7.06 (d, 1H, J=2.2 Hz), 6.86 (dd, 1H, J=7.8 Hz, J=1.5 Hz), 6.85-6.56 (m, 3H), 6.72 (d, 1H, J=8.4 Hz), 5.40 (s, 2H), 5.10 (dd, 1H, J=10.0 Hz; J=2.3 Hz), 3.04-2.87 (m, 1H), 2.78-2.65 (m, 1H), 2.24-2.10 (m, 1H), 2.08-1.89 (m, 1H).

Workup

  1. customProduct was purified by column chromatography (CH2Cl2

Sources & evidence

ORD record
ord-5e56bcc02fd04f0b865bae0ba699904c
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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