Nitric Acid → HCID 45121157, compound

HRID 362668Notes

Reaction equation

[C:1]1(=[O:9])[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH2:2]1.S(=O)(=O)(O)O.[N+:15]([O-])([OH:17])=[O:16].[K+].[Br-]>O>[N+:15]([C:6]1[CH:7]=[CH:8][C:3]2[CH2:2][C:1](=[O:9])[C:4]=2[CH:5]=1)([O-:17])=[O:16]

Participants

Conditions

Temperature: -10 °C

Procedure

Benzocyclobutenone (3.0 g, 25.42 mmol) was added slowly to concentrated sulfuric acid (6 mL) at -5° C.-0° C. with vigorous stirring. The resulting solution was further cooled to -10° C. and the mixture of concentrated sulfuric acid (3 mL) and nitric acid (70%, d 1.42, 2.0 mL) was added at such a rate that the solution temperature remained between -10° C. and -5° C. After the completion of addition of nitrating solution, stirring continued for 10 min. The reaction mixture was then poured into an ice slurry (30 g of ice in 30 mL of water). The product which precipitated out as yellow solids from water was collected by suction filtration and washed with water twice, aqueous sodium carbonate solution (10%) twice, and water twice consecutively. The solid product was recrystallized from methanol to give white fine crystals: 3.44 g (83.1%); mp 126°-127° C.; IR (KBr) 1342, 1522, 1785 cm-1 ; 1H NMR (200 MHz, CDCl3) 4.16 (s, 2H), 7.95 (d, 1H), 8.22 (s, 1H), 8.51 (d, 1H); MS (EI, m/e, relative intensity %) 163 (M+., 99.3), 135 (M+. -CO, 39.3), 89 (135 -.NO2, 100).

Workup

additionwas added at such a rate that the solution temperature
customremained between -10° C. and -5° C
additionAfter the completion of addition of nitrating solution
customThe product which precipitated out as yellow solids from water
filtrationwas collected by suction filtration
washwashed with water twice
customThe solid product was recrystallized from methanol
customto give white fine crystals

Sources & evidence

ORD record: ord-41c3cf52496a4c419e1509a65e004399
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05869693

Reaction notes

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