Nitric Acid → HCID 20304550, compound

HRID 236952Notes

Reaction equation

HRID 236952 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[O:5][C:4]2[C:13]([CH2:21][CH2:22][CH3:23])=[C:14]3[C:19](=[CH:20][C:3]1=2)[CH2:18][CH2:17][CH2:16][CH2:15]3.[N+:24]([O-])([OH:26])=[O:25].O>S(=O)(=O)(O)O>[N+:24]([C:20]1[C:3]2[C:2](=[O:1])[CH:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[O:5][C:4]=2[C:13]([CH2:21][CH2:22][CH3:23])=[C:14]2[C:19]=1[CH2:18][CH2:17][CH2:16][CH2:15]2)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 2801521HCID 2801521, compound

Product 1

HCID 20304550HCID 20304550, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Ethyl 6,7,8,9-tetrahydro-4-oxo-10-propyl-4H-naphtho[2,3-b]pyran-2-carboxylate (9.4 g) was dissolved in concentrated sulphuric acid (100 ml) and cooled to room temperature, and fuming nitric acid (3 ml) was added dropwise, with stirring. The resulting mixture was stirred for a further 3 hours and then poured into water (2 l). The resulting yellow semi-solid was extracted into ether. The organic layer was washed with water, dried (sodium sulphate) and evaporated to give a yellow solid of moderately pure ethyl 6,7,8,9-tetrahydro-5-nitro-4-oxo-10-propyl-4H-naphtho[2,3-b]pyran-2-carboxylate (8.5 g; 79%). An analytically pure sample (5 g) was obtained on recrystallisation from cyclohexane, mp 140°-2°.

Workup

  1. stirringThe resulting mixture was stirred for a further 3 hours
  2. extractionThe resulting yellow semi-solid was extracted into ether
  3. washThe organic layer was washed with water
  4. dry with materialdried (sodium sulphate)
  5. customevaporated

Sources & evidence

ORD record
ord-7a41ed18f78e4cf4ab7762b8d9527f6d
Source dataset
uspto-grants-1979_06
Patent number
US04159273

Reaction notes

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