Sodium Nitrate → HCID 12012757, compound

HRID 1884401Notes

Reaction equation

HRID 1884401 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[N+:18]([O-])([O-:20])=[O:19].[Na+]>FC(F)(F)C(O)=O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:10][C:11]=2[N+:18]([O-:20])=[O:19])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 11299248HCID 11299248, compound

Product 1

HCID 12012757HCID 12012757, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 2 (467 mg, 2 mmol) was added to a stirred solution of sodium nitrate (170 mg, 2 mmol) in trifluoroacetic acid (5 mL) and the mixture was stirred at rt for 4 h. The solution was poured into ice-cold water (100 mL) and extracted with EtOAc. The combined organic phases were washed with saturated aq. NaHCO3 and brine, dried and evaporated. Recrystallization (EtOAc-hexanes) afforded 16 as orange needles (395 mg, 71%), mp 136-137° C.; IR: νmax/cm−1 1740, 1670, 1530; 1H NMR: δH (90 MHz) 7.52 (br s, 1H), 7.36 (br s, 1H), 4.23 (t, J=8.3 Hz, 2H), 3.70 (s, 3H), 3.62 (s, 2H), 3.20 (t, J=8.3 Hz, 2H) and 2.24 (s, 3H). Anal. Calcd for C13H14N2O5: C, 62.94; H, 6.27; N, 4.59. Found: C, 63.00; H, 6.16; N, 4.59.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic phases were washed with saturated aq. NaHCO3 and brine
  3. customdried
  4. customevaporated
  5. customRecrystallization (EtOAc-hexanes)

Sources & evidence

ORD record
ord-7bc2e4a903a54da5a49094a76659e277
Source dataset
uspto-grants-2004_07
Patent number
US06765014B1

Reaction notes

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