2-Fluoro-5-nitroaniline → HCID 675675, compound

HRID 633433Notes

Reaction equation

HRID 633433 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[F:7][C:8]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:9]=1[NH2:10].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[F:7][C:8]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:9]=1[NH:10][C:4]([CH:1]1[CH2:3][CH2:2]1)=[O:5]

Participants

6

Reactant 3

HCID 677852-Fluoro-5-nitroanilineHCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 675675HCID 675675, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Cyclopropanecarbonyl chloride (5.4 mL, 60 mmol) was added dropwise over 5 min to a stirred solution of 2-fluoro-5-nitroaniline (1.56 g, 10.0 mmol) and solid NaHCO3 (7.65 g, 90 mmol) in DCM (50 mL) at room temperature under nitrogen. The mixture was stirred overnight then diluted with DCM (50 mL) and H2O (100 mL) and stirred for 30 min. The aqueous and organic layers were partitioned and the aqueous layer extracted with DCM (2×50 mL). The combined organic layers were dried (Na2SO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was dry-loaded onto silica gel and purified by column chromatography on silica gel using EtOAc/heptane (1:9 to 4:6) as eluent to give the product (2.2 g, 98% yield) as a solid.

Workup

  1. stirringstirred for 30 min
  2. customThe aqueous and organic layers were partitioned
  3. extractionthe aqueous layer extracted with DCM (2×50 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed under vacuum
  7. customto leave a crude residue
  8. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3a707b0e9b80473cbb423051269d71e4
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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