Nitric Acid → HCID 5291935, compound

HRID 566881Notes

Reaction equation

HRID 566881 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([CH3:13])[C:8]([OH:12])=[CH:9][CH:10]=2)[O:5][C:4](=[O:14])[CH:3]=1.[N+:15]([O-])([OH:17])=[O:16]>S(=O)(=O)(O)O>[N+:15]([C:9]1[CH:10]=[C:11]2[C:6](=[C:7]([CH3:13])[C:8]=1[OH:12])[O:5][C:4](=[O:14])[CH:3]=[C:2]2[CH3:1])([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 53565972H-1-Benzopyran-2-one, 7-hydroxy-4,8-dimethyl-

Product 1

HCID 5291935HCID 5291935, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

4,8-Dimethyl-7-hydroxycoumarin (7.50 g, 39.4 mmoles) was dissolved in 75 ml concentrated sulfuric acid at room temperature and chilled to −20° C. before the addition of chilled nitrating mixture (3 ml concentrated nitric acid added to 9 ml concentrated sulfuric acid). Stirring was continued for three hours at −20° C. with the mixture allowed to warm before pouring into ice. Bright yellow crystals were filtered, washed with water and dried to recover 7.50 g (81% yield). The product was recrystallized from ethanol to give yellow green crystals: mp 229.5-231.5° C.; 1H-nmr (dimethyl sulfoxide-d6):δ 2.29 (s, 3H), 2.41 (s, 3H), 6.37 (s, 1H), 8.19 (s, 1H), 11.30 (s, 1H); 13C-nmr (dimethyl sulfoxide-d6):δ 8.8, 18.0, 112.4, 112.9, 115.1, 119.9, 132.8, 152.9, 154.2, 155.1, 159.0; ms: (EI) m/z (relative intensity) 236 (M+, 23), 235 (M+, base) 207 (84), 77 (30).

Workup

  1. temperatureto warm
  2. additionbefore pouring into ice
  3. filtrationBright yellow crystals were filtered
  4. washwashed with water
  5. customdried
  6. customto recover 7.50 g (81% yield)
  7. customThe product was recrystallized from ethanol
  8. customto give yellow green crystals

Sources & evidence

ORD record
ord-3c016c7b46194f44b89cab072ebf89de
Source dataset
uspto-grants-2001_01
Patent number
US06177424B1

Reaction notes

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