Sodium Methoxide → HCID 86745620, compound

HRID 1029438Notes

Reaction equation

HRID 1029438 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[C:11]2[C:6](=[C:7](OC)[CH:8]=[CH:9][CH:10]=2)[N:5]=1.[CH3:25][O-:26].[Na+]>CO>[CH3:25][O:26][CH2:3][C:4]1[CH:13]=[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 19900496HCID 19900496, compound

Product 1

HCID 86745620HCID 86745620, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

800 mg (=2.2 mmol) of 2-chloromethyl-8-methoxy-4(2-methylbenz-ylamino)quinoline hydrochloride were refluxed with 1.2 g (=22 mmol) of sodium methylate in 30 ml of absolute methanol for 5 hours The mixture was concentrated in a rotary evaporator, ethyl acetate was added, and the mixture was extracted several times with K2CO3 solution. The residue after drying over Na2SO4 and removal of the solvent was recrystallized from ethanol 200 mg (=28%) of 8-methoxy..2-methoxymethyl-4-(2-methylbenzylamino)quinoline of melting point 194-195° C. were obtained

Workup

  1. concentrationwas concentrated in a rotary evaporator, ethyl acetate
  2. additionwas added
  3. extractionthe mixture was extracted several times with K2CO3 solution
  4. dry with materialThe residue after drying over Na2SO4 and removal of the solvent
  5. customwas recrystallized from ethanol 200 mg (=28%) of 8-methoxy

Sources & evidence

ORD record
ord-70977c5acea94a358f1a1a6f87b07f65
Source dataset
uspto-grants-1992_04
Patent number
US05102892

Reaction notes

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