Methyl p-toluenesulfonate → HCID 22266863, compound

HRID 1163035Notes

Reaction equation

HRID 1163035 reaction equation
N[C:2]1C=CC2C(=C(OC)C=CC=2)N=1.C(OC(=O)C)(=O)C.[CH3:21][C:22]1[O:23][C:24]2[C:25]([N:36]=1)=[N:26][C:27]1[C:28]([O:34][CH3:35])=[CH:29][CH:30]=[CH:31][C:32]=1[CH:33]=2.[S:37]([C:42]1[CH:48]=[CH:47][C:45]([CH3:46])=[CH:44][CH:43]=1)([O:40]C)(=[O:39])=[O:38]>N1C=CC=CC=1>[NH2:36][C:25]1[C:24]([OH:23])=[CH:33][C:32]2[C:27](=[C:28]([O:34][CH3:35])[CH:29]=[CH:30][CH:31]=2)[N:26]=1.[S:37]([C:42]1[CH:48]=[CH:47][C:45]([CH3:46])=[CH:44][CH:43]=1)([O-:40])(=[O:39])=[O:38].[CH3:21][CH:22]1[NH+:36]=[C:25]2[N:26]([CH3:2])[C:27]3[C:28]([O:34][CH3:35])=[CH:29][CH:30]=[CH:31][C:32]=3[CH:33]=[C:24]2[O:23]1

Participants

7

Reactant 4

HCID 6645Methyl p-toluenesulfonateHCID 7918Acetic AnhydrideHCID 22266814HCID 22266814, compoundHCID 222668208-Methoxyquinolin-2-amine

Product 2

HCID 22266863HCID 22266863, compoundHCID 178488368HCID 178488368, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino-3-hydroxy-8-methoxyquinoline is prepared according to M. Y. Chu-Moyer (as above) starting from 2-amino-8-methoxyquinoline. This compound is treated with 3 equivalents of acetic anhydride in pyridine, and the reaction mixture is heated from room temperature to 120° C. and stirred overnight. The 2-methyl-5-methoxyoxazolo[4,5-b]quinoline thus generated is then heated with 3 equivalents of methyl tosylate at 70° C. for 8 hours to give the desired product.

Workup

  1. temperaturethe reaction mixture is heated from room temperature to 120° C.

Sources & evidence

ORD record
ord-61abb1e3c4dd4db2a61f968bb0d8fd51
Source dataset
uspto-grants-2010_10
Patent number
US07820824B2

Reaction notes

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