Nitric Acid → HCID 20096586, compound

HRID 2221109Notes

Reaction equation

HRID 2221109 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])=[CH:8][CH:7]=1)[CH3:2].[N+:24]([O-])([OH:26])=[O:25]>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:23])[NH:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])=[CH:10][C:11]=1[N+:24]([O-:26])=[O:25])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 69272449HCID 69272449, compound

Product 1

HCID 20096586HCID 20096586, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

(4-Phtalimido-phenyl)-carbamic acid ethyl ester (99.0 g, 0.32 mol) is suspended in glacial acetic acid (1.5 L) and heated to 90° C. Fuming nitric acid (17.2 mL, 0.41 mol) is added dropwise over 30 minutes at 90-95° C. The reaction mixture is then stirred at 100° C. for 1 hour and cooled to ambient temperature. Crystallised solids are filtered off and washed with glacial acetic acid (500 mL), water (1 L) and diethylether (1 L) on the filter, then dried in vacuo to furnish 101 g (90%) of the title compound as a yellow solid. LC/MS (m/z) 355.0 (MH+); tR=3.34 min. 1H NMR (DMSO-d6): 1.25 (t, 3H); 4.16 (q, 2H); 7.81 (m, 2H); 7.93 (ddd, 2H); 7.99 (ddd, 2H); 6.15 (dd, 1H); 9.99 (s, 1H, NH).

Workup

  1. temperaturecooled to ambient temperature
  2. customCrystallised solids
  3. filtrationare filtered off
  4. washwashed with glacial acetic acid (500 mL), water (1 L) and diethylether (1 L) on the filter
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a598cc1295104ee0a46377594a01657e
Source dataset
uspto-grants-2008_05
Patent number
US07368472B2

Reaction notes

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