1-(Benzyloxy)-2,3-dinitrobenzene → 3-(Benzyloxy)benzene-1,2-diamine

HRID 1650671Notes

Reaction equation

HRID 1650671 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[C:10]=1[N+:18]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Ni]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[C:10]=1[NH2:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 139713581-(Benzyloxy)-2,3-dinitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 44012883-(Benzyloxy)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of O-benzyl-2,3-dinitrophenol (Description 12) (4.5 g) in ethanol (300 ml) was hydrogenated at atmospheric pressure over Raney nickel (2 g) until uptake of hydrogen ceased. The solution was filtered and evaporated to dryness in vacuo to afford unstable O-benzyl-2,3-diaminophenol which was immediately heated with phenylacetic acid (20 g) at 140°-150° C. for 3 h. The product was heated under reflux with 5N-hydrochloric acid (70 ml) for 3 h and neutralised with 10% sodium carbonate. The mixture was extracted with chloroform, and the organic layer washed with 10% sodium carbonate, water and dried (Na2SO4). The recovered product was chromatographed on Silica Gel 60 (250 g) eluting with ethylacetate-chloroform (1:19) to afford the title compound (1.6 g), m.p. 172°-174° C. (ethanol/ether).

Workup

  1. filtrationThe solution was filtered
  2. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-59d1cbcfd74041f0b552ef46e15ed389
Source dataset
uspto-grants-1990_05
Patent number
US04925853

Reaction notes

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