2-Nitrotoluene → HCID 10399255, compound

HRID 1428801Notes

Reaction equation

HRID 1428801 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].[CH2:17]([O:19][C:20](=[O:24])[CH:21](Cl)[CH3:22])[CH3:18].C([O-])(O)=O.[Na+]>CN(C)C=O.C(OC(=O)C)C>[CH3:7][C:8]1[CH:13]=[C:12]([CH:21]([CH3:22])[C:20]([O:19][CH2:17][CH3:18])=[O:24])[CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15]

Participants

7

Reactant 4

HCID 69442-NitrotolueneHCID 10807Ethyl 2-chloropropionateHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 10399255HCID 10399255, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of added potassium tertiary butoxide (2.05 g, 18.3 mmol) in dimethylformamide (10 mL) were slowly added the mixture of 1-methyl-2-nitrobenzene (1 g, 7.29 mmol) and ethyl-2-chloropropionate (0.98 mL, 7.70 mmol) at −30° C. The reaction mixture was stirred for 10 min and warmed to room temperature. The residue was dissolved with ethylacetate and neutralized with NaHCO3. The organic layer was washed with water two times, then dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. Ethyl 2-(3-methyl-4-nitrophenyl)propanoate (1.20 g) was obtained as 70% yield.

Workup

  1. washThe organic layer was washed with water two times
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate removed in vacuo
  5. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-4e3659b07bf34b9fb8224279697ec43e
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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