Allyl bromide → HCID 19390564, compound

HRID 1756504Notes

Reaction equation

HRID 1756504 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([OH:14])=[O:13])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:21](Br)[CH:22]=[CH2:23]>CN(C=O)C>[CH2:23]([O:13][C:12]([C:4]1[CH:3]=[C:2]([NH2:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)=[O:14])[CH:22]=[CH2:21]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 225039574-Aminoquinoline-2-carboxylic acid

Product 1

HCID 19390564HCID 19390564, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Amino-2-quinoline carboxylic acid (800 mg, 4.2 mmol) in DMF (10 ml) and K2CO3 (1.17 g, 8.5 mmol) was stirred at ambient temperature in the presence of allyl bromide (1.47 ml, 17 mmol) for 24 hours. The solvent was evaporated and the crude residue purified by subjecting to silico-gel chromatography, eluting with petroleum ether ethyl acetate 1/1) to give 2-allyloxycarbonyl-4-amino-quinoline (170 mg, NMR (CDCls): δ4.75-5 (m, 4H); 5.2-5.0 (m, 2H); 5.9-6.35 (m, 1H); 7.35-8.3 (m, 5H).

Workup

  1. customThe solvent was evaporated
  2. customthe crude residue purified
  3. washeluting with petroleum ether ethyl acetate 1/1)

Sources & evidence

ORD record
ord-4cffe37e8603424c81bf6b93264f10b7
Source dataset
uspto-grants-1995_08
Patent number
US05441949

Reaction notes

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