Methylamine → HCID 22113355, compound

HRID 864600Notes

Reaction equation

HRID 864600 reaction equation
[Cl:1][C:2]1[C:20]([N:21]([CH2:36]C(OCC)=O)[C:22](=[O:35])[CH2:23][N:24]2C(=O)C3=CC=CC=C3[C:25]2=[O:34])=[CH:19][CH:18]=[C:17]([Cl:42])[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.CN>ClCCl.CO>[Cl:1][C:2]1[C:20]([N:21]2[CH2:36][C:25](=[O:34])[NH:24][CH2:23][C:22]2=[O:35])=[CH:19][CH:18]=[C:17]([Cl:42])[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

Participants

5

Reactant 2

HCID 6329MethylamineHCID 22112989HCID 22112989, compound

Product 1

HCID 22113355HCID 22113355, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To the solution of 8-[2,6-dichloro-3-[N-ethoxycarbonylmethyl-N-(phthalimidoacetyl)amino]benzyloxy]-2-methylquinoline (527 mg) in dichloromethane (5.3 ml) was added 30% solution of methylamine in methanol (2 ml) at ambient temperature. After stirring for 24 hours, the reaction mixture was evaporated in vacuo. The residue was purified by flash column chromatography (silica gel 50 ml) eluting with dichloromethane/methanol (20/1, V/V) and by crystallizing from isopropyl ether to give 8-[2,6- dichloro-3-(2,5-dioxopiperazin-1-yl)benzyloxy]-2-methylquinoline (187 mg) as colorless crystals.

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. customThe residue was purified by flash column chromatography (silica gel 50 ml)
  3. washeluting with dichloromethane/methanol (20/1, V/V)
  4. customby crystallizing from isopropyl ether

Sources & evidence

ORD record
ord-d90de35ec5254b479589095580664da1
Source dataset
uspto-grants-1996_10
Patent number
US05563162

Reaction notes

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