Methyl 3,5-dinitro-4-(4-methoxyphenoxy)-benzoate → Methyl 3,5-diamino-4-(4-methoxyphenoxy)benzoate

HRID 564839

반응식

HRID 564839 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([N+:23]([O-])=O)[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[C:7]([O:9][CH3:10])=[O:8])([O-])=O.[H][H]>C(O)(=O)C.[Pd]>[NH2:23][C:12]1[CH:11]=[C:6]([CH:5]=[C:4]([NH2:1])[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[C:7]([O:9][CH3:10])=[O:8]

참가 물질

5

반응물 2

HCID 9819693Methyl 3,5-dinitro-4-(4-methoxyphenoxy)-benzoateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 9947870Methyl 3,5-diamino-4-(4-methoxyphenoxy)benzoate수율 86%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

To a Parr shaker bottle containing a suspension of methyl 3,5-dinitro-4-(4-methoxyphenoxy)-benzoate (20.2 g; 77.5 mmol) in glacial acetic acid (80 ml) was added 10% palladium on charcoal (0.7 g). The bottle was shaken under an atmosphere of hydrogen (3 atm) until no more hydrogen was consumed. The catalyst was filtered off and the resulting solution concentrated to approximately 10 ml. The residue was dissolved in acetone (50 ml) and heated on a steam bath while water (100 ml) was added in portions. Upon cooling, medium brown needles formed which were collected by suction filtration and dried to give 7.1 g (86%) of methyl 3,5-diamino-4-(4-methoxyphenoxy)benzoate. 300 MHz 1H NMR (CDCl3) d 3.73 (s, 3H, OCH3), 3.80 (bs, 4H, ArNH2) 3.86 (s, 3H, OCH3), 6.84 (m, 4H, ArH), 6.91 (s, 2H, ArH).

후처리

  1. additionTo a Parr shaker bottle containing
  2. customwas consumed
  3. filtrationThe catalyst was filtered off
  4. concentrationthe resulting solution concentrated to approximately 10 ml
  5. dissolutionThe residue was dissolved in acetone (50 ml)
  6. temperatureheated on a steam bath while water (100 ml)
  7. additionwas added in portions
  8. temperatureUpon cooling
  9. custommedium brown needles formed which
  10. filtrationwere collected by suction filtration
  11. customdried

출처 및 근거

ORD 기록
ord-de484765b90a4e72846db3c105cf1216
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06169104A

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