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

HRID 1723558Notes

Reaction equation

HRID 1723558 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-f4e9dbf4dd8a4a90a1c980c01ecc8b13
Source dataset
uspto-grants-1989_08
Patent number
US04861880

Reaction notes

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