Nitric Acid → 7-Bromo-4-hydroxy-3-nitrocoumarin

HRID 1283315Notes

Reaction equation

HRID 1283315 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([OH:17])=[CH:11][C:12](=[O:16])[O:13]2)=[CH:8][CH:7]=1>C(Cl)(Cl)Cl>[Br:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([OH:17])=[C:11]([N+:1]([O-:4])=[O:2])[C:12](=[O:16])[O:13]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 546962297-Bromo-4-hydroxycoumarin

Product 1

HCID 547109707-Bromo-4-hydroxy-3-nitrocoumarin

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Fuming nitric acid (27 ml) was added to a stirred suspension of 7-bromo-4-hydroxycoumarin (m.p. 247.5°-248.5°; 4.18g) in chloroform (400 ml) at room temperature over 1.5 hours. After a further 1.5 hours, 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. 155°-7°, (C9H4NO5Br requires C, 37.79; H, 1.41; N. 4.90; Br, 27.94. Found: C, 37.46; H, 1.45; N, 4.78; Br, 27.93).

Workup

  1. customthe solvent was removed in vacuo at room temperature
  2. addition6N hydrochloric acid (100 ml) added to the residue
  3. filtrationFiltration
  4. customgave the product, m.p. 155°-7°, (C9H4NO5Br requires C, 37.79; H, 1.41; N. 4.90; Br, 27.94. Found: C, 37.46; H, 1.45; N, 4.78; Br, 27.93)

Sources & evidence

ORD record
ord-8ea962e6b1d041a9b171c6fddc4b0713
Source dataset
uspto-grants-1976_08
Patent number
US03974289

Reaction notes

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