Diethylamine → 1-(3-Chlorophenyl)-3-(diethylaminomethylene)-2(1H,3H)-indolone

HRID 1632663Notes

Reaction equation

HRID 1632663 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]OCC)[C:9]2=[O:21])[CH:5]=[CH:6][CH:7]=1.[CH2:22]([NH:24][CH2:25][CH3:26])[CH3:23]>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:24]([CH2:25][CH3:26])[CH2:22][CH3:23])[C:9]2=[O:21])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 537126431-(3-Chlorophenyl)-3-(ethoxymethylene)-2(1H,3H)-indolone

Product 1

HCID 540645801-(3-Chlorophenyl)-3-(diethylaminomethylene)-2(1H,3H)-indolone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(3-Chlorophenyl)-3-(ethoxymethylene)-2(1H,3H)-indolone (0.15 g, 0.5 mmole), diethylamine (5 ml, 48 mmole) and ethanol (30 ml) were combined and stirred 24 hours at 25°. The reaction mixture was concentrated in vacuo to an oil. The oil was taken up in ethyl acetate, washed with H2O and then brine, dried over MgSO4 and evaporated to yield title product which crystallized on cooling and trituration with ether/pentane, 96 mg. m.p. 74°-75.5°.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to an oil
  2. washwashed with H2O
  3. dry with materialbrine, dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-a9acc70543474ef08c2026e8fc2d3805
Source dataset
uspto-grants-1984_10
Patent number
US04476307

Reaction notes

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