Water → HCID 14724151, compound

HRID 2073216Notes

Reaction equation

HRID 2073216 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[N:12]1([NH2:21])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1.CC[O:24]CC.Cl.[C:28](=[O:31])([O-])[O-:29].[Na+].[Na+].[OH2:34]>C(O)(C)C>[C:28]([OH:29])(=[O:31])/[CH:11]=[CH:2]\[C:3]([OH:24])=[O:34].[N:12]1([NH:21][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1

Participants

7

Reactant 5

HCID 962WaterHCID 10340Sodium CarbonateHCID 691404-ChloroquinolineHCID 6432211-AminoindoleHCID 10953452Ether hydrochloride

Product 1

HCID 14724151HCID 14724151, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution prepared from 4-chloro-quinoline (5 g), 1H-indol-1-amine (5 g), 100 ml isopropanol and 1 ml saturated ether/HCl was stirred for three hours at reflux, and thereafter cooled, stirred with water, basified with sodium carbonate and extracted with dichloromethane. The organic extract was washed successively with water and saturated sodium chloride solution, dried (anhy. MgSO4), filtered and concentrated to a solid. This was purified by flash chromatography (silica, 10% ethyl acetate in dichloromethane) to give 6.5 g solid, m.p. 128° C. This was converted to the maleate salt in methanol to give 7.4 g of crystals, m.p. 207°-208° C. dec. Three grams were recrystallized from methanol/ether to give 2.6 g crystals, m.p. 209°-210° dec.

Workup

  1. temperatureat reflux
  2. temperaturecooled
  3. extractionextracted with dichloromethane
  4. extractionThe organic extract
  5. washwas washed successively with water and saturated sodium chloride solution
  6. customdried (anhy
  7. filtrationMgSO4), filtered
  8. concentrationconcentrated to a solid
  9. customThis was purified by flash chromatography (silica, 10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-8b371241a3c24b41ac46a9c19a8306bf
Source dataset
uspto-grants-1990_04
Patent number
US04916135

Reaction notes

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