Hydroxylamine → 1-Heptyl-3-Hydroxyaminocarbonyl-4-Hydroxy-2(1H)-Quinolinone

HRID 1768535Notes

Reaction equation

HRID 1768535 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([OH:18])=[C:10]([C:19](OCC)=[O:20])[C:9]1=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C[O-].[Na+].[NH2:28][OH:29]>CO>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([OH:18])=[C:10]([C:19]([NH:28][OH:29])=[O:20])[C:9]1=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 10942334Sodium MethoxideHCID 546847811-Heptyl-3-Ethoxycarbonyl-4-Hydroxy-2(1H)-Quinolinone

Product 1

HCID 547197721-Heptyl-3-Hydroxyaminocarbonyl-4-Hydroxy-2(1H)-QuinolinoneYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A round-bottomed flask was charged with the product from step (1) (493 mg, 1.49 mmole), sodium methoxide (208 mg, 3.85 mmole), hydroxylamine (278 mg, 4.0 mmole) and methanol (10 mL). The reaction was stirred for 24 hrs and the precipitated product was collected by filtration, washed with water and dried in vacuo to give the title compound (40% yield). That the expected product was obtained was confirmed by the spectral data: M.S. (FAB): m/e 319 (M·+ +H); NMR (DMSO-d6): δ8.25 (1 H, d), 7.85 (1H, dd), 7.7 (1H, d), 7.45 (dd), 4.4 (2H, m, CH2N), 2.95 (br s, exchangeable protons), 1.8 (2H, m), 1.55 (8H, m), 0.95 (3H, t, CH3).

Workup

  1. filtrationthe precipitated product was collected by filtration
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-a02f7f26d1704287b518a871f70c9d64
Source dataset
uspto-grants-1995_01
Patent number
US05378694

Reaction notes

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