Hydrochloric Acid → HCID 178482356, compound

HRID 1644558Notes

Reaction equation

HRID 1644558 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:12][CH3:13])=[N:7][CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1.Cl>C(O)(=O)C.[Fe]>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([CH:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=3)[C:8]([NH:12][CH3:13])=[N:7][CH2:6]2)=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 1784823576-chloro-N-methyl-4-(4-nitrophenyl)-3,4-dihydroisoquinolin-1-amine

Product 1

HCID 178482356HCID 178482356, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

135.2 mg of iron powder were added to a solution of 255 mg of 6-chloro-1-methylamino-4-(4-nitrophenyl)-3,4-dihydroisoquinoline in 4.5-5 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. Amorphous product.

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

Sources & evidence

ORD record
ord-0d613b64bb67411bab97e9af69dc6a53
Source dataset
uspto-grants-2012_02
Patent number
US08124621B2

Reaction notes

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