Hydrochloric Acid → 3-amino-4-(2-chlorophenyl)-7,8-dihydro-6H-cyclopenta[g]quinoline

HRID 36931Notes

Reaction equation

HRID 36931 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][C:14]3[CH2:20][CH2:19][CH2:18][C:15]=3[CH:16]=2)[N:11]=[CH:10][C:9]=1[N+:21]([O-])=O.Cl.O.O.[Sn](Cl)Cl.[OH-].[Na+]>O.O1CCOCC1>[NH2:21][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:8]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])=[CH:16][C:15]1[CH2:18][CH2:19][CH2:20][C:14]=1[CH:13]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 199365644-(2-chlorophenyl)-7,8-dihydro-3-nitro-6H-cyclopenta[g]quinoline

Product 1

HCID 152316043-amino-4-(2-chlorophenyl)-7,8-dihydro-6H-cyclopenta[g]quinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 4-(2-chlorophenyl)-7,8-dihydro-3-nitro-6H-cyclopenta[g]quinoline (4.50 g), dioxane (45 ml) and concentrated hydrochloric acid (15 ml) was added tin(II) chloride dihydrate (9.5 g) followed by stirring at room temperature for one hour. The reaction mixture was then diluted with water, made strongly alkaline with 6N NaOH and extracted with chloroform. The extract was washed with water and dried (MgSO4) and the solvent was distilled off to give crystals of 3-amino-4-(2-chlorophenyl)-7,8-dihydro-6H -cyclopenta[g]quinoline. The crystals were collected by filtration and washed with isopropyl ether (3.45 g, 83.3%). Recrystallization from ether gave colorless needles, mp 179°-180° C.

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-47beefc3f35941e7ba81b4d84a794ef6
Source dataset
uspto-grants-1995_05
Patent number
US05418239

Reaction notes

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