p-Toluenesulfonic acid → 2-Methyloxazolo[4,5-b]quinoline

HRID 488855Notes

Reaction equation

HRID 488855 reaction equation
[NH2:1][C:2]1[C:11]([OH:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][C:14](C)(C)C([O-])([O-])[O-].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)(=O)C>[CH3:13][C:14]1[O:12][C:11]2[C:2]([N:1]=1)=[N:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=1[CH:10]=2

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 21927715TrimethylorthoacetateHCID 222668072-Amino-3-hydroxyquinoline

Product 1

HCID 222668482-Methyloxazolo[4,5-b]quinoline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.6 g of 2-amino-3-hydroxyquinoline, 3.8 mL of trimethylorthoacetate and 0.1 g of p-toluenesulfonic acid is heated at 60° C. for 7 hours. The reaction mixture is then diluted with ethyl acetate, washed with sodium bicarbonate, and purified by column chromatography on silica gel to yield 0.28 g of 2-methyloxazolo[4,5-b]quinoline. The quinoline is heated with one equivalent of methyl tosylate at 70° C. for one hour to generate the product.

Workup

  1. washwashed with sodium bicarbonate
  2. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0c559ba4754e413aba2785d17b84691c
Source dataset
uspto-grants-2005_12
Patent number
US06974873B2

Reaction notes

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