Methane → 2-[(4-Methoxyphenyl)amino]benzoic acid

HRID 1662934

反応式

HRID 1662934 の反応式
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.Cl[C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].C(=O)([O-])[O-].[Na+].[Na+].C>O.C(O)CO>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:11]2[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1

参加物

7

反応物 4

HCID 297MethaneHCID 7732P-AnisidineHCID 83742-Chlorobenzoic AcidHCID 10340Sodium Carbonate

生成物 1

HCID 2029182-[(4-Methoxyphenyl)amino]benzoic acid収率 49.3%

試薬・触媒・溶媒 2

HCID 174Ethylene Glycol溶媒HCID 962Water溶媒2 回

反応条件

温度
125 °C

実験手順

4-Methoxyaniline (1.86 gm; 20 mmol), 2-chlorobenzoic acid (1.56 gm; 10 mmol), ethylene glycol (5 ml) and anhydrous sodium carbonate (1.1 gm; 10 mmol) were placed in a reaction vessel and stirred until effervescence ceased. Cupric chloride (100 mg; 0.75 mmol) dissolved in 2 ml of water was added to the reaction mixture which was then heated to 125° C. for 6 hours. The reaction was allowed to cool then water (30 ml) and charcoal were added. The mixture was filtered and acidified to pH 2 with conc. hydrochloric acid. The precipitate was collected by filtration, washed with water and then re-dissolved in 1M sodium hydroxide solution. Material was re-precipitated by the addition of acetic acid, filtered off, washed with aqueous acetic acid, then water and finally dried under vacuum over phosphorous pentoxide to give 1200 mg (49%) of N-(4-methoxyphenyl)anthranilic acid.

後処理

  1. additionwas added to the reaction mixture which
  2. temperatureto cool
  3. filtrationThe mixture was filtered
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. dissolutionre-dissolved in 1M sodium hydroxide solution
  7. customMaterial was re-precipitated by the addition of acetic acid
  8. filtrationfiltered off
  9. washwashed with aqueous acetic acid
  10. dry with materialwater and finally dried under vacuum over phosphorous pentoxide

出典と根拠

ORDレコード
ord-abef91a7a1624203b5bda919b96a9a39
出典データセット
uspto-grants-2011_10
特許番号
US08034558B2

関連ノート

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