Nitric Acid → HCID 85867462, compound

HRID 730320Notes

Reaction equation

HRID 730320 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:13]([OH:16])(=[O:15])=[O:14])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[N+:17]([O-])([OH:19])=[O:18]>S(=O)(=O)(O)O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:17]([O-:19])=[O:18])=[C:10]([S:13]([OH:16])(=[O:14])=[O:15])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 15279289HCID 15279289, compound2×

Product 1

HCID 85867462HCID 85867462, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

16.0 g (66 mmol) of 1-acetylindoline-6-sulfonic acid (Compound 2-2 in Scheme II) was dissolved in 160 mL of cone, sulfuric acid. The solution was cooled to 0° C. using ice/water bath. Nitric acid (90%, furming) (3.0 mL, 1.1 eqv.) was added dropwise over 10 min. The resulting pale yellow solution was stirred at 0° C. for 2 h and then slowly poured onto 200 g of ice. The crystals formed were collected by filtration and washed successively with cold water acetone and ether. Drying under vacuum over P2O5 afforded 18.2 g of the title compound. 1H MNR (d6-DMSO) δ: 8.47 (s, 1H), 7.40 (s, 1H), 5.54 (OH+H2O), 4.12 (t, J=8.5 Hz, 2H), 3.13 (t, J=8.5 HZ, 2H) and 2.17 (s, 3H). 13C NMR (d6-DMSO) δ: 169.19, 144.18, 143.17, 139.54, 133.54, 119.10, 115.23, 48,67, 26.75 and 24.01.

Workup

  1. customThe crystals formed
  2. filtrationwere collected by filtration
  3. washwashed successively with cold water acetone and ether
  4. dry with materialDrying under vacuum over P2O5

Sources & evidence

ORD record
ord-8adf7b828b744b8abad2a14b36e2fe1a
Source dataset
uspto-grants-2009_09
Patent number
US07582739B2

Reaction notes

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