Allyl Alcohol → 2-Propen-1-yl 8-nitro-6-quinolinecarboxylate

HRID 1756502Notes

Reaction equation

HRID 1756502 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([OH:3])=[O:2].[C:17]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:22]=CC=C[CH:18]=1.C(O)C=C.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:22]([O:2][C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)=[O:3])[CH:17]=[CH2:18]

Participants

6

Reactant 4

HCID 7858Allyl AlcoholHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 71401918-nitroquinoline-6-carboxylic Acid

Product 1

HCID 193905822-Propen-1-yl 8-nitro-6-quinolinecarboxylateYield 67.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-carboxy-8-nitroquinoline (5.7 g; 26 mM) in THF (70 ml) was added triphenylphosphine (8.9 g; 33.8 mM), allyl alcohol (2.3 ml; 33.8 mM) and DEAD (5.35 ml; 33.8 mM). After stirring at ambient temperature for 30 minutes, the mixture was extracted with ethyl acetate and purified by subjecting to flash chromatography, eluting with ethyl acetate/petroleum ether (40/60) to give 6-allyloxycarbonyl 8-nitroquinoline (4 g; 67.7%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. custompurified
  3. washeluting with ethyl acetate/petroleum ether (40/60)

Sources & evidence

ORD record
ord-121fab8c8d4e45e0bac07c5a2f2e9efe
Source dataset
uspto-grants-1995_08
Patent number
US05441949

Reaction notes

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