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

HRID 1650671노트

반응식

HRID 1650671 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 935Nickel촉매HCID 702Ethanol용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-59d1cbcfd74041f0b552ef46e15ed389
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04925853

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