Chloroform → 8-(3-Amino-2,6-dimethylbenzyloxy)-2-methylquinoline

HRID 1699172Notes

Reaction equation

HRID 1699172 reaction equation
[CH3:1][C:2]1[C:20]([N+:21]([O-])=O)=[CH:19][CH:18]=[C:17]([CH3:24])[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.O.NN.C(Cl)(Cl)Cl>CO>[NH2:21][C:20]1[C:2]([CH3:1])=[C:3]([C:17]([CH3:24])=[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 3

HCID 6212ChloroformHCID 24654Hydrazine hydrate (1:1)HCID 183218528-(2,6-Dimethyl-3-nitrobenzyloxy)-2-methylquinoline

Product 1

HCID 183218048-(3-Amino-2,6-dimethylbenzyloxy)-2-methylquinolineYield 78.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 8-(2,6-dimethyl-3-nitrobenzyloxy)-2-methylquinoline (2.34 g), ferric chloride (70.6 mg) and carbon (70.6 mg) in methanol (35 ml) was added hydrazine monohydrate (1.09 g) at 65° C., and the mixture was refluxed for 2 hours. Methanol (20 ml) was added thereto, and the mixture was refluxed for 1 hour. After cooling chloroform was added thereto, and the resulting precipitates were filtered off. The filtrate was concentrated and the residue was dissolved in chloroform. The solution was washed with saturated sodium bicarbonate solution, water and brine, dried over magnesium sulfate and concentrated. The residue was crystallized with ethyl acetate to give 8-(3-amino-2,6-dimethylbenzyloxy)-2-methylquinoline (1.67 g) as a pale brown crystal.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperaturethe mixture was refluxed for 1 hour
  3. additionwas added
  4. customthe resulting precipitates
  5. filtrationwere filtered off
  6. concentrationThe filtrate was concentrated
  7. dissolutionthe residue was dissolved in chloroform
  8. washThe solution was washed with saturated sodium bicarbonate solution, water and brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was crystallized with ethyl acetate

Sources & evidence

ORD record
ord-71dd8e115c8a4e3f8d7478c62fde2609
Source dataset
uspto-grants-2002_02
Patent number
US06344462B1

Reaction notes

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