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

HRID 1858037ノート

反応式

HRID 1858037 の反応式
[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]

参加物

5

反応物 2

HCID 9819693Methyl 3,5-dinitro-4-(4-methoxyphenoxy)-benzoateHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒

実験手順

To a Parr shaker bottle containing a suspension of methyl 3,5-di-nitro-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).

後処理

  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

出典と根拠

ORDレコード
ord-2b072b2a193d4258ad386e408e8f4d25
出典データセット
uspto-grants-2000_11
特許番号
US06150407

反応ノート

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