Hydrochloric Acid → 4-(4-Ethenylphenoxy)benzene-1,3-diamine

HRID 896730Notes

Reaction equation

HRID 896730 reaction equation
[CH:1]([C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:9]=2[N+:17]([O-])=O)=[CH:5][CH:4]=1)=[CH2:2].[Sn](Cl)Cl.Cl.[OH-].[K+]>C(O)C.O1CCCC1>[CH:1]([C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=2[NH2:17])=[CH:5][CH:4]=1)=[CH2:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24479Stannous ChlorideHCID 22352092HCID 22352092, compound

Product 1

HCID 223520904-(4-Ethenylphenoxy)benzene-1,3-diamineYield 64.2%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

1-[4-Vinylphenoxy]-2,4-dinitrobenzene (9.0 g, 31 mmol) was dissolved in 100 ml ethanol/tetrahydrofuran (1:1). In succession, tin(II)chloride (70.9, 310 mmol), and 10N HCl (37.7 ml, 377 mmol) were added. The solution was stirred at room temperature 16 h. The reaction mixture was poured into a separatory funnel containing 150 ml ice-cold water followed by the addition of 20% KOH (ice-cold, 629 g). The mixture was extracted with ether (3×100 ml). The combined organic phases were washed with water (3×100 ml) and brine, dried with solid MgSO4 and concentrated. Column chromotography yielded 4.5 g product. The product was crystallized from 40% ethyl acetate in hexane. 1H NMR (CDCl3): 7.32 (d, 2H, J=8.5 Hz), 6.88 (d, 2H, J=8.6 Hz), 6.73 (d, 1H, J=8.3 Hz), 6.66 (dd, 1H, J=17.3, 11.9 Hz), 6.15 (d, 1H, J=2.9 Hz), 6.08 (dd, 1H, J=2.4, 8.2 Hz), 5.61 (dd, 1H, J=17.6 Hz, 0.8 Hz), 5.14 (d, 1H, J=10.9 Hz), 4.38 (br s, 4H).

Workup

  1. additionThe reaction mixture was poured into a separatory funnel
  2. extractionThe mixture was extracted with ether (3×100 ml)
  3. washThe combined organic phases were washed with water (3×100 ml) and brine
  4. dry with materialdried with solid MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f42a84669f6a408a8e6392ed8cddc067
Source dataset
uspto-grants-2005_07
Patent number
US06919404B2

Reaction notes

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