Dichloromethane → HCID 22113128, compound

HRID 1604521Notes

Reaction equation

HRID 1604521 reaction equation
[Cl:1][C:2]1[C:22]([N+:23]([O-])=O)=[CH:21][CH:20]=[C:19]([Cl:26])[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]=[C:11]2[O:17][CH3:18].[Sn](Cl)Cl.[OH-].[Na+].ClCCl>CO>[NH2:23][C:22]1[C:2]([Cl:1])=[C:3]([C:19]([Cl:26])=[CH:20][CH:21]=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]=[C:11]2[O:17][CH3:18]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 22112963HCID 22112963, compound

Product 1

HCID 22113128HCID 22113128, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 8-(2,6-dichloro-3-nitrobenzyloxy)-4-methoxy-2-methylquinoline (1.75 g) in methanol (17 ml) was added tin (II) chloride (3.37 g) at ambient temperature. The mixture was refluxed for 1 hour. After cooling, the mixture was adjusted to pH 10 with 1 N sodium hydroxide solution. To this mixture was added dichloromethane (50 ml) and the precipitate was removed by filtration. The filtrate was extracted with dichloromethane twice. The organic layer was washed with water and brine. After dried over magnesium sulfate, the solvent was removed in vacuo to give 8-(3-amino-2,6-dichlorobenzyloxy)-4-methoxy-2-methylquinoline (1.16 g) as a colorless powder.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. temperatureAfter cooling
  3. customthe precipitate was removed by filtration
  4. extractionThe filtrate was extracted with dichloromethane twice
  5. washThe organic layer was washed with water and brine
  6. dry with materialAfter dried over magnesium sulfate
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-18e0c8ceb6104e8497ab7659bd93f00f
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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