Isobutyryl chloride → HCID 66684475, compound

HRID 2370970Notes

Reaction equation

HRID 2370970 reaction equation
[CH:1]1([C:4]2[CH:9]=[C:8]([F:10])[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:5]=2[NH2:14])[CH2:3][CH2:2]1.C([O-])(O)=O.[Na+].[CH3:20][CH:21]([CH3:25])[C:22](Cl)=[O:23]>ClCCl.O>[CH:1]1([C:4]2[CH:9]=[C:8]([F:10])[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:5]=2[NH:14][C:22](=[O:23])[CH:21]([CH3:25])[CH3:20])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 62325Isobutyryl chlorideHCID 516892Sodium BicarbonateHCID 58065782HCID 58065782, compound

Product 1

HCID 66684475HCID 66684475, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-cyclopropyl-4-fluoro-5-nitrobenzenamine (as described in WO2011068898) (1.98 g, 10.09 mmol, 1 equiv) in dichloromethane (50 mL) at room temperature, was added NaHCO3 (7.65 g, 90.84 mmol, 9 equiv), followed by 2-methylpropanoyl chloride (6.34 mL, 60.56 mmol, 6 equiv). The reaction mixture was stirred overnight. The reaction mixture was taken in water, and the layers were separated. The organic layer was washed with ice-cold 1N NaOH 2×, brine 1×, dried over Na2SO4, and concentrated to dryness. The crude product was absorbed onto silica gel and purified by flash chromatography and eluted with hex:EtOAc=100:0 to 50%-70% EtOAc using 10% EtOAc increments to afford N-(2-cyclopropyl-4-fluoro-5-nitrophenyl)isobutyramide (2.04 g, 84%) as a light-brown solid.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with ice-cold 1N NaOH 2×, brine 1×
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe crude product was absorbed onto silica gel
  6. custompurified by flash chromatography
  7. washeluted with hex

Sources & evidence

ORD record
ord-b934856b2d8e43ef8c6e8fac9d43f61d
Source dataset
uspto-grants-2014_04
Patent number
US08710223B2

Reaction notes

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