Ammonium Acetate → 6-[2-Methyl-4-(6-methyl-pyridin-2-yl)-oxazol-5-yl]-quinoline

HRID 917679Notes

Reaction equation

HRID 917679 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8](=O)[CH:9]([O:20][C:21](=O)[CH3:22])[C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:29]>C(O)(=O)C>[CH3:22][C:21]1[O:20][C:9]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)=[C:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=2)[N:29]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 68883979Acetic acid 2-(6-methyl-pyridin-2-yl)-2-oxo-1-quinolin-6-yl-ethyl ester

Product 1

HCID 688849096-[2-Methyl-4-(6-methyl-pyridin-2-yl)-oxazol-5-yl]-quinoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of acetic acid 2-(6-methyl-pyridin-2-yl)-2-oxo-1-quinolin-6-yl-ethyl ester (83 mg, 0.26 mmol), ammonium acetate (200 mg, 2.6 mmol, 10 equiv) in acetic acid (4 mL) is heated to 105° C. for 3 hours. The resulting reaction mixture is concentrated in vacuo, and reverse phase high pressure liquid chromatography (a gradient from 5-30% acetonitrile in 0.1% aqueous formic acid) provides 6-[2-Methyl-4-(6-methyl-pyridin-2-yl)-oxazol-5-yl]-quinoline.

Workup

  1. customThe resulting reaction mixture
  2. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-bf669aa677c441918ba74066d7f016ce
Source dataset
uspto-grants-2007_09
Patent number
US07273936B2

Reaction notes

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