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

HRID 2196129Notes

Reaction equation

HRID 2196129 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-642b9ec688704249bb080a6eed3eb890
Source dataset
uspto-grants-2012_12
Patent number
US08338415B2

Reaction notes

Loading…