Sodium Carbonate → 2'-Methyl-4-nitro-biphenyl-2-ylamine

HRID 1596305ノート

反応式

HRID 1596305 の反応式
Br[C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[Na+].[Na+].[C:18]1([CH3:27])[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC=CC=1>[CH3:27][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 826072-Bromo-5-nitroanilineHCID 27332672-Methylphenyl boronic acid

生成物 1

HCID 185464992'-Methyl-4-nitro-biphenyl-2-ylamine収率 91%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 241Benzene溶媒

実験手順

A mixture of 1.0 g (4.6 mmol) 2-bromo-5-nitroaniline, 20 ml benzene, 10 ml 2 N sodium carbonate solution, 159 mg (0.14 mmol) tetrakis (triphenylphosphine)-palladium(0) and 725 mg (5.07 mmol) o-tolylboronic acid was heated under argon at 60° for 20 hrs. After cooling to room temperature, the aqueous phase was separated and washed twice with toluene. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/hexane 2:1) to yield 950 mg (91%) of 2′-methyl-4nitro-biphenyl-2-ylamine as a pale yellow oil, MS (EI): 228 (M+).

後処理

  1. temperaturewas heated under argon at 60° for 20 hrs
  2. customthe aqueous phase was separated
  3. washwashed twice with toluene
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified by chromatography (SiO2, CH2Cl2/hexane 2:1)

出典と根拠

ORDレコード
ord-e43e5290f49d41ee9846e2ef78dbd3d2
出典データセット
uspto-grants-2001_09
特許番号
US06291465B1

反応ノート

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