1-Butanol → Quinoline

HRID 1490021Notes

Reaction equation

HRID 1490021 reaction equation
OC1C(=O)C(=O)C=1O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.CC1C(C)(C)[C:28]2[C:23](=[C:24]3C=CC=C[C:25]3=[CH:26][CH:27]=2)[N+:22]=1[CH2:36][CH2:37][CH3:38].C(O)CCC>C1C=CC=CC=1>[N:22]1[C:23]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 2631-ButanolHCID 17913Squaric acidHCID 86751431HCID 86751431, compound

Product 1

HCID 7047QuinolineYield 89.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 0.80 g of 3,4-dihydroxy-3-cyclobutene-1,2-dione, 5.99 g of 2,3,3-trimethyl1-propyl-3H-benzoindolium p-toluenesulfonate obtained in Reference Example 1, 1.64 g of quinoline, 30 ml of butanol and 30 ml of benzene was stirred under reflux for 11 hours. After the reaction solution was concentrated, 30 ml of ethanol was added to the residue, followed by heating for 30 minutes. After cooling, the crystals were filtered off and dried in vacuo to give 2.07 g of Compound 2.

Sources & evidence

ORD record
ord-fb1863e77abd41d5a36f2bb464de8753
Source dataset
uspto-grants-1997_10
Patent number
US05681685

Reaction notes

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