Hydrochloric Acid → HCID 24769744, compound

HRID 1644560Notes

Reaction equation

HRID 1644560 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]([CH3:14])[CH3:13])=[N:7][CH2:6][CH:5]2[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=1.Cl>C(O)(=O)C.[Fe]>[ClH:1].[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([CH:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=3)[C:8]([N:12]([CH3:14])[CH3:13])=[N:7][CH2:6]2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66773007HCID 66773007, compound

Product 1

HCID 24769744HCID 24769744, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

100 mg of iron powder were added to a solution of 195 mg of 6-chloro-1-dimethylamino-4-(4-nitrophenyl)-3,4-dihydroisoquinoline in 3.5 ml of glacial acetic acid and then 1.8 ml of concentrated hydrochloric acid were added dropwise, and the mixture was boiled under reflux conditions for 2 hours. The solvent was removed by distillation, and the residue was mixed with water and made alkaline with 2N NaOH. This aqueous phase was extracted with ethyl acetate and purified by MPLC chromatography using an MPRC cartridge with a mixture of 10 parts by volume of ethyl acetate, 5 parts by volume of n-heptane, 5 parts by volume of dichloromethane, 5 parts by volume of methanol and 1 part by volume of concentrated aqueous ammonia solution. After removal of the solvent in a Rotavapor, the viscous amorphous residue was treated in ethyl acetate with ethereal hydrogen chloride solution, and the crystalline solid was filtered off.

Workup

  1. customThe solvent was removed by distillation
  2. additionthe residue was mixed with water
  3. extractionThis aqueous phase was extracted with ethyl acetate
  4. custompurified by MPLC chromatography
  5. additionwith a mixture of 10 parts by volume of ethyl acetate, 5 parts by volume of n-heptane, 5 parts by volume of dichloromethane, 5 parts by volume of methanol and 1 part by volume of concentrated aqueous ammonia solution
  6. customAfter removal of the solvent in a Rotavapor
  7. additionthe viscous amorphous residue was treated in ethyl acetate with ethereal hydrogen chloride solution
  8. filtrationthe crystalline solid was filtered off

Sources & evidence

ORD record
ord-d6e632b149ca49a690bb80bd003a1593
Source dataset
uspto-grants-2012_02
Patent number
US08124621B2

Reaction notes

Loading…