2,4-Dinitro-1-(2-phenylchroman-6-yloxy)-benzene → 5-Amino-2-(2-phenylchroman-6-yloxy)-aniline

HRID 31230Notes

Reaction equation

HRID 31230 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[O:20][CH:19]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:18][CH2:17]2)([O-])=O.C1(C2CCC3C(=CC=C(OC4C=CC=CC=4N)C=3)O2)C=CC=CC=1>C(O)(=O)C.[Zn]>[NH2:10][C:8]1[CH:7]=[CH:6][C:5]([O:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[O:20][CH:19]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:18][CH2:17]3)=[C:4]([CH:9]=1)[NH2:1]

Participants

5

Reactant 2

HCID 179785452,4-Dinitro-1-(2-phenylchroman-6-yloxy)-benzeneHCID 179785582-(2-Phenylchroman-6-yloxy)-aniline

Product 1

HCID 179784735-Amino-2-(2-phenylchroman-6-yloxy)-aniline

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

2,4-Dinitro-1-(2-phenylchroman-6-yloxy)-benzene (0.04 g) was dissolved in 12 ml of glacial acetic acid and zinc (0.131 g) was added. The reaction stirred at room temperature for 30 minutes. Workup was done as described for 2-(2-phenylchroman-6-yloxy)-aniline in Example 29. Product was purified by column chromatography (CH2Cl2:Et3N /96:4 as the eluant). 1H-NMR (300 MHz; d6-DMSO): δ 7.48-7.28 (m, 5H), 6.74 (d, 1H, J=8.8 Hz), 6.63 (dd, 1H, J=8.8 Hz, J=2.9 Hz), 6.57 (d, 1H, J=2.8 Hz), 6.49 (d, 1H, J=8.4 Hz), 6.02 (d, 1H, J=2.6 Hz), 5.81 (dd, 1H, J=8.4 Hz, J=2.6 Hz), 5.03 (dd, 1H, J=10.0 Hz, J=2.3 Hz), 4.62 (s, 2H), 4.48 (s, 2H), 2.99-2.82 (m, 1H), 2.71-2.57 (m, 1H), 2.20-2.06 (m, 1H), 2.03-1.86 (m, 1H)

Workup

  1. customProduct was purified by column chromatography (CH2Cl2

Sources & evidence

ORD record
ord-6d5b998aea2f402e82cd9bbe1fc616b5
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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