1,4-Dioxane hydrochloride → HCID 59441795, compound

HRID 1014408Notes

Reaction equation

HRID 1014408 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([F:16])=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=2)[CH2:6][CH2:5]1)(=O)C.Cl.O1CCOCC1>O1CCCC1.CO>[F:16][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][C:10]=1[N+:13]([O-:15])=[O:14])[NH:4][CH2:5][CH2:6]2

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59441933HCID 59441933, compound

Product 1

HCID 59441795HCID 59441795, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-acetyl-5-fluoro-6-nitro-2,3-dihydro-1H-indole (1.22 g, 5.44 mmol) and 4.0 M HCl/dioxane (6.80 ml, 27.2 mmol) in tetrahydrofuran (50 ml) and methanol (100 ml) was heated overnight at 50 C. The reaction was quenched with saturated NaHCO3 (200 ml), solvent removed, aqueous layer extracted with dichloromethane (250 ml), organic layer adsorbed to silica gel and purified by LC (20-75% ethyl acetate/hexanes) to afford the indoline (0.9 g, 91%). ESIMS (M+H)+=183.

Workup

  1. customThe reaction was quenched with saturated NaHCO3 (200 ml), solvent
  2. customremoved
  3. extractionaqueous layer extracted with dichloromethane (250 ml), organic layer
  4. custompurified by LC (20-75% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-40861e2d713c42fb9f754c99b1908dc1
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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