Potassium Nitrate → HCID 25139889, compound

HRID 1669181Notes

Reaction equation

HRID 1669181 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[CH2:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:17][C:18](=[O:20])[CH3:19])[CH:14]=2)[CH2:9]1)[CH3:7]>>[CH2:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([N+:1]([O-:4])=[O:2])=[C:13]([NH:17][C:18](=[O:20])[CH3:19])[CH:14]=2)[CH2:9]1)[CH3:7]

Participants

3

Reactant 2

HCID 24434Potassium NitrateHCID 25138871HCID 25138871, compound

Product 1

HCID 25139889HCID 25139889, compoundYield 50%

Conditions

Temperature
0 °C

Procedure

KNO3 (1.33 g, 13.2 mmol) was added in small portions, over 10 min, to a stirred solution of acetamide 246 (2.45 g, 12.0 mmol) in CH2SO4 (50 mL) at 0° C. and the reaction mixture was stirred at 0° C. for a further 45 min. The mixture was poured onto ice, made basic with cNH3 and extracted with DCM (3×100 mL). The solvent was evaporated to give a brown oil which was purified by chromatography on neutral Al2O3, eluting with a gradient (0-20%) of EtOAc/pet. ether, to give nitroacetamide 247 (1.49 g, 50%) as a yellow solid: mp EtOAc/pet. ether) 85-87° C.; 1H NMR δ 10.43 (br s, 1H, NH), 8.62 (s, 1H, H-7), 8.03 (s, 1H, H-4), 3.96 (s, 2H, CH2N), 3.92 (s, 2H, CH2N), 2.79 (q, J=7.2 Hz, 2H, CH2N), 2.28 (s, 3H, COCH3), 1.21 (t, J=7.2 Hz, 3H, CH3); HRMS (FAB+) calcd for C12H16N3O3 (MH+) m/z 250.1192, found 250.1195. Anal. calcd for C12H15N3O3: C, 57.8; H, 6.0; N, 16.9. Found: C, 57.9; H, 5.9; N, 16.7%.

Workup

  1. additionThe mixture was poured onto ice
  2. extractionextracted with DCM (3×100 mL)
  3. customThe solvent was evaporated
  4. customto give a brown oil which
  5. customwas purified by chromatography on neutral Al2O3
  6. washeluting with a gradient (0-20%) of EtOAc/pet. ether

Sources & evidence

ORD record
ord-f3c00b2ee8a645049f1f017a36f9885a
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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