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

HRID 1662934

반응식

HRID 1662934 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 174Ethylene Glycol용매HCID 962Water용매2회

반응 조건

온도
125 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-abef91a7a1624203b5bda919b96a9a39
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08034558B2

연결된 노트

불러오는 중…