Carbazole → HCID 14724156, compound

HRID 2073217Notes

Reaction equation

HRID 2073217 reaction equation
[CH:1]1[C:13]2[N:12]([NH2:14])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:15]1[C:27]2[NH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2C=CC=1.[Cl:28]C1C2C(=CC=CC=2)N=CC=1.CCOCC.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C.O>[ClH:28].[N:26]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([NH:14][N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[CH:15][CH:27]=1

Participants

8

Reactant 5

HCID 6854CarbazoleHCID 10340Sodium CarbonateHCID 691404-ChloroquinolineHCID 2762079H-carbazol-9-amineHCID 10953452Ether hydrochloride

Product 1

HCID 14724156HCID 14724156, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 9H-carbazol-9-amine (11 g, as an unquantified mixture with carbazole) and 4-chloroquinoline (10 g) in 100 ml isopropanol acidified with ether/HCl was refluxed for seven hours, and thereafter cooled, stirred with water, basified with sodium carbonate and extracted with ethyl acetate. The organic extract was washed successively with water and saturated sodium chloride solution, dried (anhy. MgSO4), filtered and concentrated to 20 g solid. This material was converted to the hydrochloride salt in methanol/ether to give 6 g solid, m.p. >260°. Three grams were recrystallized from methanol/ether to give 2.6 g white needles, dec. 300°-302°.

Workup

  1. temperaturewas refluxed for seven hours
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed successively with water and saturated sodium chloride solution
  6. customdried (anhy
  7. filtrationMgSO4), filtered
  8. concentrationconcentrated to 20 g solid

Sources & evidence

ORD record
ord-0520bc837ff84cca91632a93c0e68902
Source dataset
uspto-grants-1990_04
Patent number
US04916135

Reaction notes

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