Chromic Acid → HCID 21931842, compound

HRID 1244015Notes

Reaction equation

HRID 1244015 reaction equation
C[O:2][C:3](=[O:20])[CH:4]([OH:19])[C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][C:11](=[O:16])[N:12]2[CH3:15])=[CH:7][C:6]=1[O:17][CH3:18].[Cr](O)(O)(=O)=O>CC(C)=O.S(=O)(=O)(O)O.O>[CH3:18][O:17][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:5]=1[C:4](=[O:19])[C:3]([OH:20])=[O:2])[N:12]([CH3:15])[C:11](=[O:16])[CH2:10][CH2:9]2

Participants

5

Reactant 2

HCID 24425Chromic AcidHCID 69654550HCID 69654550, compound

Product 1

HCID 21931842HCID 21931842, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21910475Sulfuric acid hydrate (1:1)Solvent

Procedure

To a solution of 1.2 g (0.0043 m) of hydroxy-(6-methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl) acetic acid methyl ester dissolved in 40 ml of acetone was added dropwise 1.6 ml of a 2.67 m solution of chromic acid in sulfuric acid/H2O (Jones reagent). The mixture was stirred for 90 minutes at room temperature. The acetone was decanted from the green precipitate and evaporated. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate. The ethyl acetate solution was dried with sodium sulfate and evaporated to yield 1.0 g (84%) of (6-methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydro quinolin-7-yl)-oxo acetic acid as a yellow amorphous solid. 1H NMR (CDCl3) δ 2.60 (m, 2H), 2.90 (m, 2H), 3.20 (s, 3H), 3.80 (s, 3H), 3.90 (s, 3H), 6.80 (s, 1H), 7.40 (s, 1H). Mass spectrum: m/e=277.9 (p+1). TLC (3/1 chloroform/ethyl acetate) Rf=0.8.

Workup

  1. customThe acetone was decanted from the green precipitate
  2. customevaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialThe ethyl acetate solution was dried with sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-1cc3b138562d49f4a2b209ed14eb5bb4
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

Loading…