Nitric Acid → HCID 18695456, compound

HRID 1870215Notes

Reaction equation

HRID 1870215 reaction equation
[O:1]=[C:2]1[C:11](=[O:12])[NH:10][C:9]2[C:4](=[CH:5][C:6]([F:13])=[CH:7][CH:8]=2)[N:3]1[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19].[N+:24]([O-])([OH:26])=[O:25]>S(=O)(=O)(O)O>[O:1]=[C:2]1[C:11](=[O:12])[NH:10][C:9]2[C:4](=[CH:5][C:6]([F:13])=[C:7]([N+:24]([O-:26])=[O:25])[CH:8]=2)[N:3]1[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 18695420HCID 18695420, compound

Product 1

HCID 18695456HCID 18695456, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

δ: 1.16 (6H, d, J=6.1 Hz), 1.60-1.62 (4H, m), 2.32 (2H, t, J=6.7 Hz), 4.01-4.08 (2H, m), 4.87 (1H, q, J=6.1 Hz), 7.01-7.05 (1H, m), 7.18 (1H, dd, J=5.5, 8.6 Hz), 7.32 (1H, dd, J=2.7, 11 Hz), 12.0 (1H, s). 4) In 10 ml of concentrated sulfuric acid cooled on an ice-methanol bath, 1.96 g (6.07 mmol) of isopropyl 5-[2,3-dioxo-7-fluoro-1,2,3,4-tetrahydroquinoxalin-1-yl]valerate was dissolved under stirring. To the resulting mixture, 300 μl of fuming nitric acid was added dropwise at -5° C. or lower, followed by stirring for 30 minutes. The reaction mixture was poured into ice water. The insoluble matter so precipitated was collected by filtration, washed with water and dried under reduced pressure to give 2.06 g (93%) of isopropyl 5-[2,3-dioxo-7-fluoro-6-nitro-1,2,3,4-tetrahydroquinoxalin-1-yl]valerate.

Workup

  1. stirringby stirring for 30 minutes
  2. customThe insoluble matter so precipitated
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-c28d440264c9481d991b9570868879a7
Source dataset
uspto-grants-2000_08
Patent number
US06096743

Reaction notes

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