Fuming sulfuric acid → Acenaphtho[1,2-b]quinoxaline-2,5-disulfonic acid

HRID 1824650Notes

Reaction equation

HRID 1824650 reaction equation
[CH:1]1[C:10]2[C:11]3[C:20]([C:8]4[C:9]=2[C:4]([CH:5]=[CH:6][CH:7]=4)=[CH:3][CH:2]=1)=[N:19][C:18]1[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=1)[N:12]=3.O[S:22]([OH:25])(=[O:24])=[O:23].[O:26]=[S:27](=[O:29])=[O:28]>O>[CH:1]1[C:10]2[C:11]3[C:20]([C:8]4[C:9]=2[C:4]([CH:5]=[C:6]([S:22]([OH:25])(=[O:24])=[O:23])[CH:7]=4)=[CH:3][C:2]=1[S:27]([OH:29])(=[O:28])=[O:26])=[N:19][C:18]1[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=1)[N:12]=3

Participants

4

Reactant 2

HCID 24681Fuming sulfuric acidHCID 136028Acenaphtho[1,2-b]quinoxaline

Product 1

HCID 22141822Acenaphtho[1,2-b]quinoxaline-2,5-disulfonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acenaphtho[1,2-b]quinoxaline (10 g) was charged into 10% oleum (49 ml), stirredfor 30 minutes and heated at 180–190° C. for 30 hours. The reaction mixture was then diluted with water (95 ml), and the formed precipitate was filtered and washed with acetic acid (˜30 ml). The filtered cake was dried on air at 120° C. to yield 8.2 g of acenaphtho[1,2-b]quinoxaline-2,5-disulfonic acid. 1H NMR (Bruker AMX-400, DMSO-d6, δ, ppm): 7.82 (q, 2H, 3 Hz); 8.18 (q, 2H, 3 Hz); 8.24–8.36 (broad s, 2H); 8.62 (s, 4H). Elemental analysis calculated for C18H10N2O6S2: C, 52.17; H, 2.43; N, 6.76; found: C, 52.02; H, 2.35; N, 6.56.

Workup

  1. temperatureheated at 180–190° C. for 30 hours
  2. filtrationthe formed precipitate was filtered
  3. washwashed with acetic acid (˜30 ml)
  4. customThe filtered cake was dried on air at 120° C.

Sources & evidence

ORD record
ord-ad85bda286234de88ea0a1b83f1ea4c1
Source dataset
uspto-grants-2006_05
Patent number
US07045177B2

Reaction notes

Loading…