Sodium Nitrite → HCID 59441694, compound

HRID 1014297Notes

Reaction equation

HRID 1014297 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)[CH3:2].[N:15]([O-:17])=[O:16].[Na+]>C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[N+:15]([O-:17])=[O:16])[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)[CH3:2]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 42597541HCID 42597541, compound

Product 1

HCID 59441694HCID 59441694, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To the solution of 6-ethoxy-3,4-dihydroquinolin-2(1H)-one (72.3 g, 0.38 mol, 1 equiv) in TFA (800 mL) was added NaNO2 (33.7 g, 0.496 mol, 1.3 equiv) at 0° C. The solution was allowed to warm to room temperature and stirring was continued for 4 hours. The mixture was poured into ice and the yellow precipitate was isolated via filtration and dried under high vacuum at 50° C. The crude product was recrystallized from ethyl acetate to afford 6-(ethyloxy)-7-nitro-3,4-dihydro-2(1H)-quinolinone (69.2 g, 77% yield). 1H NMR (400 MHz, DMSO) δ 1.31 (t, J=6.8 Hz, 3H), 2.45-2.49 (m, 2 H), 2.95 (t, 2 H, J=6.4 Hz), 4.13-4.15 (m, 2 H), 7.25 (s, 1 H), 7.34 (s, 1 H), 10.16 (bs, 1H).

Workup

  1. additionThe mixture was poured into ice
  2. customthe yellow precipitate was isolated via filtration
  3. customdried under high vacuum at 50° C
  4. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-186f679984f64be5aee42f8a9345a27e
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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