Morpholine → 1-(3-Chlorophenyl)-3-(morpholinomethylene)-2(1H,3H)-indolone

HRID 1638471Notes

Reaction equation

HRID 1638471 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[CH:17][N:18]([CH3:20])[CH3:19])[C:9]2=[O:21])[CH:5]=[CH:6][CH:7]=1.N1C[CH2:26][O:25][CH2:24]C1>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[CH:17][N:18]3[CH2:19][CH2:26][O:25][CH2:24][CH2:20]3)[C:9]2=[O:21])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8083Morpholine2×HCID 537196081-(3-Chlorophenyl)-3-(dimethylaminomethylene)-2(1H,3H)-indolone

Product 1

HCID 541400761-(3-Chlorophenyl)-3-(morpholinomethylene)-2(1H,3H)-indolone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Title product of Example A3 (0.3 g, 1.0 mmole), morpholine (0.45 ml, 5 mmole) and ethanol (10 ml) were combined and stirred 18 hours at 25°. Additional morpholine (2 ml) was added and the mixture refluxed 4 hours. The reaction mixture was evaporated in vacuo to an oil, chromatographed on silica gel (4.5 cm×18 cm) eluting with ethyl acetate, initially isolating purified title product as an oil which crystallized on standing under ether/pentane, 0.27 g; m.p. 130°-132.5° C.

Workup

  1. temperaturethe mixture refluxed 4 hours
  2. customThe reaction mixture was evaporated in vacuo to an oil
  3. customchromatographed on silica gel (4.5 cm×18 cm)
  4. washeluting with ethyl acetate
  5. custominitially isolating
  6. custompurified title product as an oil which
  7. customcrystallized

Sources & evidence

ORD record
ord-2f179b001d614d839ae38d876247de54
Source dataset
uspto-grants-1989_11
Patent number
US04879391

Reaction notes

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