N-Phenyl-p-phenylenediamine → 2,3,3a,4,5,9b-Hexahydro-4-(3-hydroxypropyl)-8-phenylamino-furano[3,2-c]quinoline

HRID 1297162

Reaction equation

HRID 1297162 reaction equation
[C:1]1([NH:7][C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[CH:16]1[CH2:20][CH2:19][CH2:18][O:17]1>O>[OH:17][CH2:16][CH2:20][CH2:19][CH:18]1[CH:19]2[CH2:20][CH2:16][O:17][CH:18]2[C:13]2[CH:14]=[C:8]([NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:9]=[CH:10][C:11]=2[NH:12]1

Participants

4

Reactant 2

HCID 7564N-Phenyl-p-phenylenediamineHCID 93002Tetrahydro-2-hydroxyfuran

Product 1

HCID 589145972,3,3a,4,5,9b-Hexahydro-4-(3-hydroxypropyl)-8-phenylamino-furano[3,2-c]quinolineYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 4-(N-phenylamino)-aniline (2 mmol), 2-hydroxy-tetrahydrofuran (6 mmol) and InCl3 (0.2-0.4 mmol) in water (5 mL) was stirred at room temperature. The reaction was monitored by TLC. After 24 h stirring at room temperature, the reaction mixture was extracted with ethyl ether (3×20 mL). Removal of solvent and flash column chromatography gave 1,2,3,4-tetrahydroquinoline derivatives in 86% yield (cis:trans=46:54).

Workup

  1. stirringAfter 24 h stirring at room temperature
  2. extractionthe reaction mixture was extracted with ethyl ether (3×20 mL)
  3. customRemoval of solvent and flash column chromatography

Sources & evidence

ORD record
ord-5fbdcdb6119e4f449b16b7b82ec26342
Source dataset
uspto-grants-2007_07
Patent number
US07250423B2

Linked notes

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