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

HRID 488511ノート

反応式

HRID 488511 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ecf4e9fef7a34951b1855939315c93e2
出典データセット
uspto-grants-2005_12
特許番号
US06972287B1

反応ノート

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