Hydrochloric Acid → 4,6-Dinitroresorcinol

HRID 2211334

반응식

HRID 2211334 반응식
C[O:2][C:3]1[C:4]([N+:13]([O-:15])=[O:14])=[CH:5][C:6]([N+:10]([O-:12])=[O:11])=[C:7]([OH:9])[CH:8]=1.CN(C)C=O.Cl.Cl>CN(C)C=O>[N+:10]([C:6]1[CH:5]=[C:4]([N+:13]([O-:15])=[O:14])[C:3]([OH:2])=[CH:8][C:7]=1[OH:9])([O-:12])=[O:11]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 2667955-Methoxy-2,4-dinitrophenol2회HCID 10920465N,N-dimethylformamide;hydrochloride

생성물 1

HCID 611584,6-Dinitroresorcinol수율 95%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

To a 100 mL round-bottom flask is added 2.14 g (10 mmol) of 5-methoxy-2,4-dinitrophenol (MDNP) and 1.31 g (12 mmol) of DMF-HCl in 30 mL of N,N-dimethylformamide (DMF). This mixture is stirred at 130° C. and monitored by High Pressure Liquid Chromatography (HPLC). After 8.5 hours essentially no MDNP is observed by HPLC. The reaction mixture is poured into 100 mL of 1N HCl, and extracted with ethyl acetate (EtOAc, 3×30 mL). The combined organics are washed with a single portion of 0.1N HCl, dried (Na2SO4) and concentrated by rotary evaporation to give crude 4,6-dinitroresorcinol (DNR) as a yellow solid (1.9 g, 95% yield): melting point (m.p.) 205° C. to 210° C., 1H NMR (CDCl3)δ11.03 (s,2H), 9.08 (s,1H), 6.82 (s,1H).

후처리

  1. extractionextracted with ethyl acetate (EtOAc, 3×30 mL)
  2. washThe combined organics are washed with a single portion of 0.1N HCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by rotary evaporation

출처 및 근거

ORD 기록
ord-764ba658150c4f60b7e970e197d8ecff
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05463129

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