Morpholine → 6-fluoro-3-(4-morpholin-4-yl-5H-furan-2-ylidene)-1,3-dihydro-indol-2-one

HRID 537903

Reaction equation

HRID 537903 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[C:12]3[CH:16]=[C:15](OC)[CH2:14][O:13]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CCO>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[C:12]3[CH:16]=[C:15]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH2:14][O:13]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 694016066-fluoro-3-(4-methoxy-5H-furan-2-ylidene)-1,3-dihydro-indol-2-one

Product 1

HCID 694011416-fluoro-3-(4-morpholin-4-yl-5H-furan-2-ylidene)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-fluoro-3-(4-methoxy-5H-furan-2-ylidene)-1,3-dihydro-indol-2-one (100 mg, 0.40 mmol) and morpholine (0.5 mL, 5.7 mmol) in 20 mL of EtOH was heated at reflux for 16 hours. The mixture was cooled to room temperature. The precipitates were filtered, rinsed with EtOH and dried in vacuum to give 6-fluoro-3-(4-morpholin-4-yl-5H-furan-2-ylidene)-1,3-dihydro-indol-2-one as a pale yellow powder. Yield: 55 mg, 45%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. filtrationThe precipitates were filtered
  4. washrinsed with EtOH
  5. customdried in vacuum

Sources & evidence

ORD record
ord-98a7013875cd4397b0f29be2640df719
Source dataset
uspto-grants-2014_10
Patent number
US08865682B2

Linked notes

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