Aniline → 5-Cyano-2-(2-phenylchroman-6-yloxy)-aniline

HRID 31232Notes

Reaction equation

HRID 31232 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[O:16][CH:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][CH2:13]3)=[C:5]([N+:26]([O-])=O)[CH:4]=1)#[N:2].NC1C=CC=CC=1.C1(C2CCC3C(=CC=C(OC4C=CC=CC=4N)C=3)O2)C=CC=CC=1>[Zn].C(O)(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[O:16][CH:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][CH2:13]3)=[C:5]([CH:4]=1)[NH2:26])#[N:2]

Participants

6

Reactant 3

HCID 6115AnilineHCID 179785464-Cyano-2-nitro-1-(2-phenylchroman-6-yloxy)-benzeneHCID 179785582-(2-Phenylchroman-6-yloxy)-aniline

Product 1

HCID 179786495-Cyano-2-(2-phenylchroman-6-yloxy)-aniline

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

4-Cyano-2-nitro-1-(2-phenylchroman-6-yloxy)-benzene (0.155 g; 0.4 mmol) was reduced to the corresponding aniline as described for 2-(2-phenylchroman-6-yloxy)-aniline in Example 29 except that 40 ml of glacial acetic acid and 0.93 g of zinc powder were used. Product was purified by column chromatography (100% CH2Cl2 as the eluant). 1H-NMR (300 MHz; d6-DMSO): δ 7.57-7.28 (m, 5H), 7.06 (d, 1H, J=2.0 Hz), 6.95-6.78 (m, 4H), 6.65 (d, 1H, J=8.3 Hz), 5.46 (s, 2H), 5.11 (dd, 1H, J=10.0 Hz, J=2.1 Hz), 3.03-2.88 (m, 1H), 2.78-2.66 (m, 1H), 2.23-2.10 (m, 1H), 2.08-1.89 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-4826321f67b84b48b1c308f63135e8e0
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

Loading…