Methyl iodide → HCID 18979095, compound

HRID 2393095Notes

Reaction equation

HRID 2393095 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[N:7]2.O1CCC[CH2:23]1.[H-].[Na+].IC>C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([N:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH3:23])=[N:7]2

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 18979069HCID 18979069, compound

Product 1

HCID 18979095HCID 18979095, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-Bromo-2-t-butyloxycarbonylamino-8-Methoxyquinoline (1.21 g) and tetrahydrofuran (20 ml) were combined at room temperature under a nitrogen atmosphere. Sodium hydride (60% dispersion in oil) (164 mg) was added and the reaction mixture stirred for 2 h whilst effervescence occurred and a yellow colour appeared. Iodomethane (0.43 ml) was then added and stirring was continued for 2 h after which time the reaction was diluted with ethyl acetate (100 ml), washed successively with water, saturated aqueous sodium bicarbonate and brine, then dried (magnesium sulphate) and evaporated in vacuo to give the title compound (1.1 g) as a yellow solid.

Workup

  1. customwere combined at room temperature under a nitrogen atmosphere
  2. stirringstirring
  3. waitwas continued for 2 h
  4. washwashed successively with water, saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8da48e0f22ce4333aa4ab2cfb937ba4a
Source dataset
uspto-grants-1998_09
Patent number
US05804588

Reaction notes

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