Coumarin → 6-Nitro-2-benzopyrone

HRID 2293002Notes

Reaction equation

[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:2]1=[O:3].[N+:12]([O-])([OH:14])=[O:13]>>[N+:12]([C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[O:1][C:2](=[O:3])[CH:4]=[CH:5]2)([O-:14])=[O:13]

Participants

Reactant 2

HCID 323Coumarin

HCID 944Nitric Acid

Product 1

HCID 759446-Nitro-2-benzopyroneYield 85%

Procedure

In greater detail, coumarin (10 g, 68 mmol) was nitrated as described in the literature with an excess of fuming nitric acid overnight at room temperature to give 6-nitrocoumarin as the only major product. The 6-nitrocoumarin exhibited the following characteristics: Yield 85%. 1H NMR (DMSO-d6): 8.74 (d, J=3 Hz, 1H), 8.42 (dd, J=3, 9 Hz, 1H), 8.24 (d, J=10 Hz, 1H), 7.63 (d, J=9 Hz, 1H), 6.70 (d, J=10 Hz, 1H).

Workup

customat room temperature

Sources & evidence

ORD record: ord-727777900f9043069023ac7f03f51d3f
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686243

Reaction notes

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