P-Xylene → HCID 21107316, compound

HRID 1765547Notes

Reaction equation

HRID 1765547 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)C=C.[CH3:15][C:16]1C=CC(C)=C[CH:21]=1>>[CH2:21]([C:6]1[C:5]([OH:4])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2)[CH:16]=[CH2:15]

Participants

3

Reactant 2

HCID 7809P-XyleneHCID 21107330HCID 21107330, compound2×

Product 1

HCID 21107316HCID 21107316, compoundYield 72%

Procedure

A solution of 6-allyloxyquinoline (intermediate 4) (1.14 g, 6.2 mmol) in p-xylene (30 ml) was allowed to reflux for 3 days. The organic solvent was removed under vacuum. Chromatography (30% hexanes-ethyl acetate) afforded 0.82 g (72%) of 5-allyl-quinolin-6-ol as a white solid: mp 162–164° C. Elemental Analysis for C12H11NO: Calculated: C, 77.81; H, 5.99; N, 7.56. Found: C, 77.82; H, 5.99; N, 7.45.

Workup

  1. temperatureto reflux for 3 days
  2. customThe organic solvent was removed under vacuum

Sources & evidence

ORD record
ord-7bce2f69661e47f28817a5592de1d5e9
Source dataset
uspto-grants-2007_06
Patent number
US07227023B2

Reaction notes

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