Acetic Acid → HCID 178481576, compound

HRID 1612760Notes

Reaction equation

HRID 1612760 reaction equation
C(O)(=O)C.[CH3:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([OH:16])=[CH:8][C:7]1=[O:17].[N:18]([O-])=[O:19].[Na+].CO>O.C(OCC)(=O)C>[CH3:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[C:8](=[N:18][OH:19])[C:7]1=[O:17]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 23668193Sodium NitriteHCID 546864364-Hydroxy-N-methylcarbostyril

Product 1

HCID 178481576HCID 178481576, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Glacial acetic acid (2.7 ml) was added with stirring to a solution of 1-methyl-4-hydroxy-2(1H)-quinolinone (1.75 gm, see G. M. Copploa, J. Org. Chem., 41, 825, (1976), already cited above) and sodium nitrite (0.8 gm) in a solvent mixture consisting of methanol (17.5 ml), ethyl acetate (20 ml) and water (10 ml) under nitrogen atmosphere. The reaction mixture was stirred for 1.5 hrs at room temperature and the organic solvents were then removed under reduced pressure. The resulting suspension was filtered and the solid washed with water to give the title compound. That the expected product was obtained was confirmed by the spectral data: MS: m/e 204 (M.+); NMR (DMSO): δ3.44 (s, 3H, CH3 --N), 15.34 (br, 1H, =NOH) ppm.

Workup

  1. customthe organic solvents were then removed under reduced pressure
  2. filtrationThe resulting suspension was filtered
  3. washthe solid washed with water

Sources & evidence

ORD record
ord-5d59c93169fe485fb44ef5666fb93295
Source dataset
uspto-grants-1993_03
Patent number
US05190956

Reaction notes

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