Chloride → HCID 10615970, compound

HRID 1604589Notes

Reaction equation

HRID 1604589 reaction equation
[CH3:1][O:2][C:3]1[C:21]([N+:22]([O-])=O)=[CH:20][CH:19]=[C:18]([O:25][CH3:26])[C:4]=1[CH2:5][O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([CH3:17])[CH:13]=[CH:12]2.[Cl-].O.NN>CO>[NH2:22][C:21]1[C:3]([O:2][CH3:1])=[C:4]([C:18]([O:25][CH3:26])=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([CH3:17])[CH:13]=[CH:12]2

Participants

5

Reactant 3

HCID 312ChlorideHCID 24654Hydrazine hydrate (1:1)2×HCID 10784308HCID 10784308, compound

Product 1

HCID 10615970HCID 10615970, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of 8-[2,6-dimethoxy-3-nitrobenzyloxy]-2-methylquinoline (2.28 g), ferrric chloride (68 mg), carbon (68 mg) and methanol (34 ml) was added hydrazine monohydrate (1.25 ml) at 60° C., and the mixture was refluxed for 4 hours. Ferric chloride (68 mg), carbon (68 mg), hydrazine monohydrate (1.25 ml) and methanol (10 ml) was further added, and the mixture was refluxed overnight. Insoluble materials were filtered off, and the filtrate was concentrated. The residue was dissolved in chloroform, and the solution was washed with saturated sodium bicarbonate solution, water and brine, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (chloroform-methanol) and crystallized with methanol to give 8-[3-amino-2,6-dimethoxybenzyloxy]-2-methylquinoline (1.33 g) as pale brown crystals.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. temperaturethe mixture was refluxed overnight
  3. filtrationInsoluble materials were filtered off
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in chloroform
  6. washthe solution was washed with saturated sodium bicarbonate solution, water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (chloroform-methanol)
  10. customcrystallized with methanol

Sources & evidence

ORD record
ord-aaa87711dbbf4c9d94b4fa86c268f073
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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