Potassium Nitrate → HCID 58134715, compound

HRID 1396115Notes

Reaction equation

HRID 1396115 reaction equation
[F:1][C:2]1[C:3]([F:25])=[C:4]2[O:9][CH2:8][C:7]3([CH2:13][CH2:12][O:11][CH2:10]3)[N:6]3[CH:14]=[C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:16](=[O:19])[C:17]([CH:18]=1)=[C:5]23.[N+:26]([O-])([O-:28])=[O:27].[K+]>OS(O)(=O)=O>[F:1][C:2]1[C:3]([F:25])=[C:4]2[O:9][CH2:8][C:7]3([CH2:13][CH2:12][O:11][CH2:10]3)[N:6]3[CH:14]=[C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:16](=[O:19])[C:17]([C:18]=1[N+:26]([O-:28])=[O:27])=[C:5]23

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 58134861HCID 58134861, compound

Product 1

HCID 58134715HCID 58134715, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 9′,10′-difluoro-7′-oxospiro[oxolane-3,3′(2H)-[7H]pyrido[1,2,3-de][1,4]benzoxazine]-6′-carboxylate (2.90 g, 8.26 mmol) in concentrated H2SO4 (40 mL) was treated portion wise at 0° C. with solid KNO3 (1.17 g, 11.6 mmol). After stirring at 0° C. for 2 h, the reaction mixture was poured into ice-water and the resulting precipitate was collected by filtration, washed with water and dried to yield ethyl 9′,10′-difluoro-8′-nitro-7′-oxospiro[oxolane-3,3′(2′H)-[7H]pyrido-[1,2,3-de][1,4]benzoxazine]-6′-carboxylate (3.20 g, 98%) as a colorless solid. 1H-NMR (400 MHz, DMSO-d6) δ1.26 (3H, t, J=7.3 Hz), 2.41-2.46 (2H, m), 3.78 (1H, d, J=10.4 Hz), 3.92-3.98 (1H, m), 4.09-4.14 (1H, m), 4.21-4.29 (3H, m), 4.62 (1H, d, J=11.6 Hz), 4.72 (1H, d, J=11.6 Hz), 8.53 (1H, s).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-cc6df70faef342ff856a211e1cab1b8c
Source dataset
uspto-grants-2014_12
Patent number
US08901112B2

Reaction notes

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