Water → HCID 19592526, compound

HRID 613459Notes

Reaction equation

HRID 613459 reaction equation
[CH2:1]([O:3][C:4]([CH:6](C(OCC)=O)[C:7]1[C:16]2[C:11](=[C:12]([N+:17]([O-:19])=[O:18])[CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[Br:20])=[O:5])[CH3:2].[Cl-].[Li+].O>CS(C)=O>[Br:20][C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:7]=1[CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 19592542HCID 19592542, compound

Product 1

HCID 19592526HCID 19592526, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-[bis(ethoxycarbonyl)methyl]-3-bromo-8-nitroquinoline (316 mg), lithium chloride (65.1 mg), water (13.8 mg) in dimethyl sulfoxide was stirred for 20 minutes at 130° C. The mixture was partitioned between ethyl acetate and water, and the organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give 3-bromo-4-ethoxycarbonylmethyl-8-nitroquinoline (236.8 mg).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-eaea2e2ab3f643b5a7fe9716c4ba2f53
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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