Nitric Acid → HCID 25140617, compound

HRID 1669077Notes

Reaction equation

HRID 1669077 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:12]=2)[CH2:7]1>C(O)(C(F)(F)F)=O>[CH3:5][CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]([N+:1]([O-:4])=[O:2])=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:12]=2)[CH2:7]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 25140616HCID 25140616, compound

Product 1

HCID 25140617HCID 25140617, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of nitric acid (70%, 3.2 mL, 50.3 mmol) in TFA (5 mL) was added dropwise to a stirred solution of acetamide 91 (3.93 g, 16.8 mmol) in TFA (40 mL) and the solution stirred at 20° C. for 2 h. The solution was poured into ice/water (400 mL) and stirred for 30 min. The precipitate was filtered, washed with water (3×30 mL), and dried. The solid was purified by chromatography, eluting with 10% EtOAc/pet. ether, to give nitroacetamide 92 (3.79 g, 96%) as a red solid: mp (EtOAc/pet. ether) 99-100° C.; 1H NMR δ 10.41 (br s, 1H, NH), 8.50 (s, 1H, H-7), 8.00 (s, 1H, H-4), 3.03-3.13 (m, 2H, CH2), 2.51-2.67 (m, 3H, H-2, CH2), 2.29 (s, 3H, COCH3), 1.14 (d, J=6.4 Hz, 3H, CH3); 13C NMR δ 169.0, 153.9, 139.4, 135.3, 133.7, 121.1, 117.7, 41.6, 40.2, 34.7, 25.6, 20.4. Anal. calcd for C12H14N2O3: C, 61.5; H, 6.0; N, 12.0. Found: C, 61.6; H, 6.2; N, 11.5%.

Workup

  1. stirringstirred for 30 min
  2. filtrationThe precipitate was filtered
  3. washwashed with water (3×30 mL)
  4. customdried
  5. customThe solid was purified by chromatography
  6. washeluting with 10% EtOAc/pet. ether

Sources & evidence

ORD record
ord-65e6fd8c95c64942b37947ee8671d1b0
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

Loading…