Nitric Acid → HCID 19045274, compound

HRID 1781371Notes

Reaction equation

HRID 1781371 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([CH2:12][C:11](=[O:13])[C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[O:8]2)[CH2:4][CH2:3]1.[N+:18]([O-])([OH:20])=[O:19].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>S(=O)(=O)(O)O>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([CH2:12][C:11](=[O:13])[C:10]3[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:9]=3[O:8]2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 944Nitric Acid2×HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 1233903N-methylspiro[2H-1-benzopyran-2,4'-piperidine]4(3H)-one

Product 1

HCID 19045274HCID 19045274, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

Sulfuric acid (55 ml) was cooled to 0° C. and was stirred as 3,4-dihydro-1'-methyl-spiro[2H-1-benzopyran-2,4'-piperidin]-4-one (11.56 g, 0.05 mol) was added over 20 minutes. Some gum separated. A solution of 90% nitric acid (2.5 ml, 0.0525 mol) in sulfuric acid (5 ml) was added over 20 minutes. The mixture was stirred for 2 hours at 0° C. and then for 1 hour at room temperature. A solution resulted but nitration was not complete. 90% Nitric acid (0.3 ml, 0.007 mol) was added and stirring was continued for 1 1/2 hours at room temperature. The reaction solution was poured into a mixture of ice, ethyl acetate, and sodium bicarbonate (210 g). The basic mixture was filtered, the ethyl acetate layer was separated and the aqueous layer was extracted with ethyl acetate (150 ml). The combined ethyl acetate extracts were washed with saturated NaCl, dried, filtered and concentrated in vacuo to yield 10.6 g (77%) of product

Workup

  1. additionwas added over 20 minutes
  2. customSome gum separated
  3. waitfor 1 hour at room temperature
  4. customA solution resulted
  5. stirringstirring
  6. customwas continued for 1 1/2 hours at room temperature
  7. filtrationThe basic mixture was filtered
  8. customthe ethyl acetate layer was separated
  9. extractionthe aqueous layer was extracted with ethyl acetate (150 ml)
  10. washThe combined ethyl acetate extracts were washed with saturated NaCl
  11. customdried
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f5952f2d3c1a47b8a5eff37ecec2b712
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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