Nitric Acid → HCID 136148564, compound

HRID 30974Notes

Reaction equation

HRID 30974 reaction equation
[O:1]=[S:2]1(=[O:28])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4]([C:12]2[C:13](=[O:27])[N:14]([CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[NH:15][CH:16]([CH:19]([CH3:21])[CH3:20])[C:17]=2[OH:18])=[N:3]1.[N+:29]([O-])([OH:31])=[O:30]>OS(O)(=O)=O>[OH:18][C:17]1[C:16]([CH:19]([CH3:21])[CH3:20])=[N:15][N:14]([CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[C:13](=[O:27])[C:12]=1[C:4]1[NH:5][C:6]2[CH:11]=[CH:10][C:9]([N+:29]([O-:31])=[O:30])=[CH:8][C:7]=2[S:2](=[O:1])(=[O:28])[N:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 136344237HCID 136344237, compound

Product 1

HCID 136148564HCID 136148564, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5h (0.097 g, 0.025 mmol) in conc H2SO4 (0.65 mL) cooled on ice bath was added conc HNO3 (0.10 mL). After stirring 30 min at 0° C., the reaction mixture was poured onto crushed ice (1.5 g). The resulting precipitate was collected by filtration to give 5i (0.091 g, 85%) as a yellow solid. 1H NMR (400 MHz, D6-DMSO) δ 13.90 (s, 1 H), 8.57 (d, J=2.8 Hz, 1 H), 8.49 (dd, J=9.2, 2.8 Hz, 1 H), 7.82 (d, J=8.8 Hz, 1 H), 4.11 (t, J=6.8 Hz, 2 H), 3.23 (m, 2 H), 1.61 (m, 2 H), 1.21 (d, J=8 Hz, 6 H), 0.93 (d, J=8 Hz, 6 H). MS (ESI+) m/e 450 [M+H]+.

Workup

  1. additionthe reaction mixture was poured
  2. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-a0ba4c4b41b04a58bd7284cc8a5fe849
Source dataset
uspto-grants-2008_09
Patent number
US07425552B2

Reaction notes

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