Potassium Carbonate → Methyl 3-cyano-3-(6-methoxy-3-nitropyridin-2-yl)propanoate

HRID 527457Notes

Reaction equation

HRID 527457 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9][C:10]#[N:11])[C:6]([N+:12]([O-:14])=[O:13])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]([O:25][CH3:26])=[O:24]>C(#N)C>[C:10]([CH:9]([C:7]1[C:6]([N+:12]([O-:14])=[O:13])=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]=1)[CH2:22][C:23]([O:25][CH3:26])=[O:24])#[N:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 6395106-Methoxy-3-nitropyridine-2-acetonitrile

Product 1

HCID 89514634Methyl 3-cyano-3-(6-methoxy-3-nitropyridin-2-yl)propanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under argon, 2-(6-methoxy-3-nitropyridin-2-yl)acetonitrile (500 mg, 2.59 mmol) was dissolved in acetonitrile (11 mL) in a flame dried round-bottom flask. Two equivalents of anhydrous potassium carbonate (0.72 g, 5.18 mmol) were added to this solution, and methyl 2-bromoacetate (245 μL, 2.59 mmol) was introduced dropwise. The reaction mixture was stirred at room temperature until the starting materials were consumed, approximately four hours. The crude material was combined with CH2Cl2 and inorganic debris was filtered off using a phase separator syringe equipped with a sodium sulfate drying cartridge. The filter cake was washed with small quantities of CH2Cl2 and all organic filtrates were collected and combined. The organic solvents were evaporated in vacuo at 40° C. and the resulting viscous dark brownish oil either directly used in the next reaction step or purified by flash chromatography on a short silica-gel column (ethyl acetate/hexane gradient) prior to its further chemical reaction. C11H11N3O5, Mr=265.22; 1H NMR (400 MHz, DMSO-d6) d: 3.15-3.29 (m, 2H), 3.64 (s, 3H), 3.99 (s, 3H), 5.22 (t, J=7.2 Hz, 1H), 7.08 (d, J=9.2 Hz, 1H), 8.48 (d, J=8.8 Hz, 1H); LCMS (ESI) tR: 1.98 min (96-100%, UV220, UV254, ELSD), m/z: 266.2 [M+1]+.

Workup

  1. additionwas introduced dropwise
  2. customwere consumed, approximately four hours
  3. filtrationwas filtered off
  4. customequipped with a sodium sulfate drying cartridge
  5. washThe filter cake was washed with small quantities of CH2Cl2
  6. customall organic filtrates were collected
  7. customThe organic solvents were evaporated in vacuo at 40° C.
  8. customthe resulting viscous dark brownish oil either directly used in the next reaction step
  9. custompurified by flash chromatography on a short silica-gel column (ethyl acetate/hexane gradient)
  10. customto its further chemical reaction

Sources & evidence

ORD record
ord-41b284c2e7ad4576aae87386296676a3
Source dataset
uspto-grants-2016_05
Patent number
US09346803B2

Reaction notes

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