Dimethylformamide → N-Propyl-9-fluorene-carboxamide

HRID 963021Notes

Reaction equation

HRID 963021 reaction equation
[CH:1]1[C:13]2[CH:12]([C:14](O)=[O:15])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.CN(C=O)C.[CH2:28]([NH2:31])[CH2:29][CH3:30]>C(Cl)Cl.C1COCC1.C(OCC)(=O)C.O>[CH2:28]([NH:31][C:14]([CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)=[O:15])[CH2:29][CH3:30]

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 7852PropylamineHCID 65578Oxalyl chlorideHCID 748099-Carboxyfluorene

Product 1

HCID 18409341N-Propyl-9-fluorene-carboxamideYield 87%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-40 °C

Procedure

A solution of 9-fluorene carboxylic acid (20.0 g, 95 mmol) in 200 mL of CH2Cl2 was treated with oxalyl chloride (12.5 g, 105 mmol) and 0.2 mL of DMF. After 0.75 h, the mixture was concentrated under reduced pressure to give a white solid. The solid was diluted with 100 mL of THF cooled to -40° C., treated with propylamine (11.8 g, 200 mmol). The suspension was stirred for 3 h at room temperature and diluted with ethyl acetate and water. The organic fraction was dried over Na2SO4 and concentrated to a white solid. The solid purified by trituration with hot hexanes and recrystalization from hot methanol to give 17.5 g (87%) of title compound as white flakes. mp 197°-199° C.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto give a white solid
  3. dry with materialThe organic fraction was dried over Na2SO4
  4. concentrationconcentrated to a white solid
  5. customThe solid purified by trituration with hot hexanes and recrystalization from hot methanol

Sources & evidence

ORD record
ord-6d4b1fb031d041b8b074b790ff6d5c15
Source dataset
uspto-grants-1998_06
Patent number
US05760246

Reaction notes

Loading…