Nitric Acid → 4-Hydroxy-3-nitro-7-propoxy-2H-1-benzopyran-2-one

HRID 1283313Notes

Reaction equation

HRID 1283313 reaction equation
[N+:1]([O-:4])(O)=[O:2].[OH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][CH2:18][CH3:19])=[CH:13][CH:14]=2)[O:9][C:8](=[O:20])[CH:7]=1>C(Cl)(Cl)Cl>[OH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][CH2:18][CH3:19])=[CH:13][CH:14]=2)[O:9][C:8](=[O:20])[C:7]=1[N+:1]([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 547294584-Hydroxy-7-propoxy-2H-1-benzopyran-2-one

Product 1

HCID 547109744-Hydroxy-3-nitro-7-propoxy-2H-1-benzopyran-2-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Fuming nitric acid (15 ml) was added to a stirred suspension of 4-hydroxy-7-n-propoxycoumarin (m.p. 216°-8°; 3.0g) in chloroform (300 ml) at room temperature over one hour. After a further hour, the solvent was removed in vacuo and 6N hydrochloric acid (60 ml) added to the residue. Filtration and recrystallisation from ethanol gave the product, m.p. 151°-2°, (C12H11NO6 requires C, 54.34; H, 4.18; N, 5.28. Found: C, 54.38; H, 4.28; N, 5.24).

Workup

  1. waitAfter a further hour
  2. customthe solvent was removed in vacuo and 6N hydrochloric acid (60 ml)
  3. additionadded to the residue
  4. filtrationFiltration and recrystallisation from ethanol
  5. customgave the product, m.p. 151°-2°, (C12H11NO6 requires C, 54.34; H, 4.18; N, 5.28. Found: C, 54.38; H, 4.28; N, 5.24)

Sources & evidence

ORD record
ord-298425a1f2e440eda4f2ba61c7e43975
Source dataset
uspto-grants-1976_08
Patent number
US03974289

Reaction notes

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