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

HRID 333356Notes

Reaction equation

HRID 333356 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-27103d9d62a8405490e81e7596bc7bd8
Source dataset
uspto-grants-2014_11
Patent number
US08877923B2

Reaction notes

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