2-Nitro-1-(2-phenylchroman-6-yloxy)-benzene → 2-(2-Phenylchroman-6-yloxy)-aniline

HRID 31226Notes

Reaction equation

HRID 31226 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[O:17][CH:16]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:15][CH2:14]2)([O-])=O>C(O)(=O)C.[Zn]>[C:21]1([CH:16]2[CH2:15][CH2:14][C:13]3[C:18](=[CH:19][CH:20]=[C:11]([O:10][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[NH2:1])[CH:12]=3)[O:17]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 179784752-Nitro-1-(2-phenylchroman-6-yloxy)-benzene

Product 1

HCID 179785582-(2-Phenylchroman-6-yloxy)-aniline

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

2-Nitro-1-(2-phenylchroman-6-yloxy)-benzene (0.160 g) was mostly dissolved in 30 ml of glacial acetic acid. Zinc powder (1.190 g) was added in few portions and the mixture was stirred for 90 minutes at room temperature. The zinc was filtered and washed with glacial acetic acid and evaporated. The evaporation residue was taken up with toluene and evaporated again. The residue was dissolved in CH2Cl2 and washed with IM NaOH. NaOH solution was further washed with CH2Cl2. Both organic fractions were combined and dried over Na2SO4. The purification of the crude product was done by elution in CH2Cl2 through a small silica column. 1H-NMR (400 MHz; d6-DMSO): δ 7.45-7.28 (m, 5H), 6.89-6.83 (m, 1H), 6.80 (d, 1H, J=8.5 Hz), 6.77 (dd, 1H, J=8.0 Hz; J=1.7 Hz), 6.73-6.67 (m, 3H), 6.54-6.48 (m, 1H), 5.06 (dd, 1H, J=10.1 Hz; J=2.3 Hz), 4.85 (s, 2H), 2.99-2.87 (m, 1H), 2.73-2.61 (m, 1H), 2.19-2.09 (m, 1H), 2.03-1.90 (m, 1H).

Workup

  1. filtrationThe zinc was filtered
  2. washwashed with glacial acetic acid
  3. customevaporated
  4. customevaporated again
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. washwashed with IM NaOH
  7. washNaOH solution was further washed with CH2Cl2
  8. dry with materialdried over Na2SO4
  9. customThe purification of the crude product
  10. washwas done by elution in CH2Cl2 through a small silica column

Sources & evidence

ORD record
ord-eb68814033a1447eb12d84a9e77ef9c8
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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