Nitric Acid → HCID 118286578, compound

HRID 514166Notes

Reaction equation

HRID 514166 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:10][C:11]([O:13][CH3:14])=[O:12].[N:20]([O-:22])=[O:21].[Na+].[N+]([O-])(O)=O.O>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:20]([O-:22])=[O:21])[CH:6]=[CH:5][C:4]=1[N:9]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:15][C:16]([O:18][CH3:19])=[O:17]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 23668193Sodium NitriteHCID 118286579HCID 118286579, compound

Product 1

HCID 118286578HCID 118286578, compoundYield 856.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Dimethyl 2,2′-((2-methoxyphenyl) azanediyl)diacetate (1.98 g, 7.41 mmol) was dissolved in acetic acid (10 mL) at room temperature followed by sodium nitrite (51 mg, 0.74 mmol). The nitric acid (0.49 mL, 8.15 mmol) was added dropwise to reaction mixture. After stirring 1 h, the reaction mixture was poured into water (20 mL), extracted with ethyl acetate (20 ml×3), and dried over MgSO4. The residue was purified by column chromatography using Hex/EtOAc (gradient: 0 to 50% EtOAc) to afford dimethyl 2,2′-((2-methoxy-4-nitrophenyl)azanediyl)diacetate (1.98 g, 86%) as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ (ppm) 7.80 (dd, J=8.8, 2.4 Hz, 1H), 7.69 (d, J=2.4 Hz, 1H), 6.66 (d, J=8.8 Hz, 1H), 4.20 (s, 4H), 3.85 (s, 3H), 3.78 (s, 6H); LCMS (ESI) tR: 0.678 min (>99%, ELSD), m/z: 313.2 [M+1]+

Workup

  1. extractionextracted with ethyl acetate (20 ml×3)
  2. dry with materialdried over MgSO4
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-857a8e849ee546aca2633e5ff6e366e0
Source dataset
uspto-grants-2015_08
Patent number
US09103791B1

Reaction notes

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