Hydrochloric Acid → 8-(3-Amino-2,6-dichlorobenzyloxy)-2-methylquinoline dihydrochloride

HRID 581769Notes

Reaction equation

HRID 581769 reaction equation
[Cl:1][C:2]1[C:20]([N+:21]([O-])=O)=[CH:19][CH:18]=[C:17]([Cl:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2.[ClH:25]>[Fe].CO>[ClH:1].[ClH:25].[NH2:21][C:20]1[C:2]([Cl:1])=[C:3]([C:17]([Cl:24])=[CH:18][CH:19]=1)[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 104989148-(2,6-Dichloro-3-nitrobenzyloxy)-2-methylquinoline

Product 1

HCID 221131408-(3-Amino-2,6-dichlorobenzyloxy)-2-methylquinoline dihydrochloride

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 8-(2,6-dichloro-3-nitrobenzyloxy)-2-methylquinoline (1.0 g), concentrated hydrochloric acid (5.2 ml) and methanol (5.2 ml) was added iron powder (666 mg). The mixture was heated under reflux for 2 hours and stirred in an ice-water bath for 1 hour. The precipitate was collected by vacuum filtration and washed with 1N hydrochloric acid and water to give 8-(3-amino-2,6-dichlorobenzyloxy)-2-methylquinoline dihydrochloride (635 mg) as a brownish powder.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. filtrationThe precipitate was collected by vacuum filtration
  4. washwashed with 1N hydrochloric acid and water

Sources & evidence

ORD record
ord-7f2438d1be544c5fa79262a006ee782c
Source dataset
uspto-grants-1999_07
Patent number
US05922711

Reaction notes

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