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

HRID 1638473Notes

Reaction equation

HRID 1638473 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-c6ffaa92c9d34d33a52d6dc46f66b8f8
Source dataset
uspto-grants-1989_11
Patent number
US04879391

Reaction notes

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