Nitric Acid → HCID 178526409, compound

HRID 1165816Notes

Reaction equation

[OH:1][C:2]1[C:3]([OH:16])=[N:4][C:5]2[CH:6]=[CH:7][C:8]3[CH2:15][CH2:14][CH2:13][CH2:12][C:9]=3[C:10]=2[N:11]=1.[N+:17]([O-])([OH:19])=[O:18]>>[OH:1][C:2]1[C:3]([OH:16])=[N:4][C:5]2[CH:6]=[C:7]([N+:17]([O-:19])=[O:18])[C:8]3[CH2:15][CH2:14][CH2:13][CH2:12][C:9]=3[C:10]=2[N:11]=1

Participants

Reactant 2

HCID 944Nitric Acid

HCID 178516988HCID 178516988, compound

Product 1

HCID 178526409HCID 178526409, compound

Conditions

Temperature: -10 °C

Procedure

7,8,9,10-Tetrahydro-2,3-dihydroxybenzo (f) quinoxaline (0.43 g, 2 mmol) was dissolved in 5 ml of nitric acid (d 1.48) by portionwise addition, with vigorous stirring on a salt/ice - bath at -10° C. After stirring at this temperature for 2 min, the mixture was poured onto 50 ml of ice/water. The precipitate was filtered off, washed with water, a small amount of ethanol, and ether affording 0.48 g (92%) of the mononitro compound; m.p. >300° C.; IR (KBr): 1720cm-1, (C=0); 1H-NMR (DMSO-d6): 1.5-1.9 (m, 4H, 2×CH2), 2.5 - 3.0 (m, 4H, 2×CH2), 7.50 (s, 1H, H-5), 11.2 (broad s, 1H, 0H), 11.9 (broad s, 1H, 0H).

Workup

stirringAfter stirring at this temperature for 2 min
filtrationThe precipitate was filtered off
washwashed with water

Sources & evidence

ORD record: ord-6e4e7fd9864b44e880c3300035b70dcc
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04912108

Reaction notes

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