Hydrochloric Acid → 2-{4-[5-(3,4-Dichloro-phenyl)pentyl]phenylamino}-5-nitrobenzoic acid

HRID 488511노트

반응식

HRID 488511 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].F[C:22]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][C:23]=1[C:24]([OH:26])=[O:25].Cl>C1COCC1.CCCCCC.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:22]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][C:23]=3[C:24]([OH:26])=[O:25])=[CH:18][CH:19]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 2809972-Fluoro-5-nitrobenzoic acidHCID 222697754-[5-(3,4-Dichlorophenyl)pentyl]phenylamine

생성물 1

HCID 222697682-{4-[5-(3,4-Dichloro-phenyl)pentyl]phenylamino}-5-nitrobenzoic acid수율 75%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

To a cooled (−78° C.) solution of 4-[5-(3,4-dichlorophenyl)pentyl]-phenylamine (0.231 g, 0.75 mmol) in THF (2 mL), LHDMS (2.25 mL, 1 M in hexane, 2.25 mmol) was added dropwise. The reaction mixture was allowed to stir at −78° C. for 10 minutes. A solution of 2-fluoro-5-nitrobenzoic acid (0.139 g, 0.75 mmol) in THF (2 mL) was added dropwise, and this solution was stirred for 30 minutes at −78° C. The reaction mixture was allowed to gradually warm to room temperature and stir for 2 hours under N2 atmosphere. The reaction mixture was diluted with EtOAc, and acidified with 1N HCl (pH 3). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to yield a brown residue. Purification by flash chromatography (silica gel, 2% MeOH/CH2Cl2) then recrystallization with MeOH yielded 265 mg (0.56 mmol, 75%) of the desired product. mp 147-148° C.

후처리

  1. additionwas added dropwise
  2. stirringthis solution was stirred for 30 minutes at −78° C
  3. temperatureto gradually warm to room temperature
  4. stirringstir for 2 hours under N2 atmosphere
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto yield a brown residue
  9. customPurification by flash chromatography (silica gel, 2% MeOH/CH2Cl2)
  10. customrecrystallization with MeOH

출처 및 근거

ORD 기록
ord-ecf4e9fef7a34951b1855939315c93e2
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06972287B1

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