Hydrochloric Acid → 4-Chloro-2-(phenylamino)benzoic acid

HRID 1261777노트

반응식

HRID 1261777 반응식
Br[C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>C(OCCO)C.O.[Cu].[Cu-]=O>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 11430Potassium CarbonateHCID 331262-Bromo-4-chlorobenzoic acid

생성물 1

HCID 6153344-Chloro-2-(phenylamino)benzoic acid수율 72.4%

시약·촉매·용매 4

HCID 23978Copper촉매HCID 178419072HCID 178419072, 화합물촉매HCID 962Water용매HCID 8076Glycol monoethyl ether용매

반응 조건

온도
25 °C

실험 절차

A solution of 2-bromo-4-chlorobenzoic acid (25.0 g, 106.0 mmol) in 2-ethoxy ethanol (40 mL) was treated with copper powder (0.74 g, 11.6 mmol), copper (I) oxide (0.76 g, 5.3 mmol) and potassium carbonate (15.8 g, 114.0 mmol) at 25° C. under nitrogen. The reaction was stirred at 25° C. for 5 min. At this time, the reaction was treated with aniline (11.2 mL, 124 mmol) and then was heated 135° C. for 48 h. At this time, the reaction was cooled to 25° C., diluted with water (30 mL) and was acidified with a 1N aqueous hydrochloric acid solution. The resulting mixture was stirred at 25° C. overnight. At this time, the resulting precipitate was collected by filtration through a sintered glass funnel. The solids were washed with an excess amount of water (2×100 mL) and then were dried under high vacuum to afford 4-chloro-2-phenylamino-benzoic acid (19 g, 72.3%) as a brown solid. This material was used without further purification.

후처리

  1. temperaturewas heated 135° C. for 48 h
  2. temperatureAt this time, the reaction was cooled to 25° C.
  3. stirringThe resulting mixture was stirred at 25° C. overnight
  4. filtrationAt this time, the resulting precipitate was collected by filtration through a sintered glass funnel
  5. washThe solids were washed with an excess amount of water (2×100 mL)
  6. customwere dried under high vacuum

출처 및 근거

ORD 기록
ord-fb2e99f9b8704716b5132fbdfd073900
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471027B2

반응 노트

불러오는 중…