Nitric Acid → 6-Ethyl-4-hydroxy-3-nitro-2H-1-benzopyran-2-one

HRID 1283304Notes

Reaction equation

HRID 1283304 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[O:13][C:12](=[O:17])[CH:11]=[C:10]2[OH:18])[CH3:6]>C(Cl)(Cl)Cl>[CH2:5]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[O:13][C:12](=[O:17])[C:11]([N+:1]([O-:4])=[O:2])=[C:10]2[OH:18])[CH3:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 546845316-Ethyl-4-hydroxy-2H-1-benzopyran-2-one

Product 1

HCID 547376476-Ethyl-4-hydroxy-3-nitro-2H-1-benzopyran-2-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Fuming nitric acid (33 ml) was added to a stirred suspension of 6-ethyl-4-hydroxycoumarin (m.p. 216°-8°; 5.52g) in chloroform (500 ml) at room temperature over 1 hour. After standing for a further hour, the solvent was removed in vacuo at room temperature and 6N hydrochloric acid (100 ml) added to the residue. Filtration gave the product m.p. 114°-5°, (C11H9NO5 requires C, 56.17; H, 3.86 N, 5.96. Found: C, 55.86; H, 3.80; N, 5.86). Recrystallisation from benzene-petroleum ether (b.p. 40°-60°) raised the melting point to 117°-9°.

Workup

  1. waitAfter standing for a further hour
  2. customthe solvent was removed in vacuo at room temperature
  3. addition6N hydrochloric acid (100 ml) added to the residue
  4. filtrationFiltration

Sources & evidence

ORD record
ord-9ec2f93a3969404ebb2098914aa748fd
Source dataset
uspto-grants-1976_08
Patent number
US03974289

Reaction notes

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