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

HRID 488511Notes

Reaction equation

HRID 488511 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ecf4e9fef7a34951b1855939315c93e2
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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