Ethyl Acetate → 1-(3-Chlorophenyl)-3-(dimethylaminomethylene)-2(1H,3H)-indolone

HRID 1110858Notes

Reaction equation

HRID 1110858 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].COC(OC)(N(C)C)C.C(OCC)(=O)C.[Cl:24][C:25]1[CH:26]=[C:27]([N:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33][C:32]2=[O:40])[CH:28]=[CH:29][CH:30]=1>C(Cl)Cl>[Cl:24][C:25]1[CH:26]=[C:27]([N:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:33](=[CH:3][N:4]([CH3:6])[CH3:5])[C:32]2=[O:40])[CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 78373Dimethylformamide dimethyl acetalHCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 112995301-(3-Chlorophenyl)-indolin-2-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

By the procedure of Example A1, but substituting an equivalent of dimethylformamide dimethylacetal for the dimethylacetamide dimethylacetal, using first methylene chloride and then 7.5% ethyl acetate in methylene chloride in chromatography and recrystallization from ether-pentane, 1-(3-chlorophenyl)-2(1H,3H)-indolone (10 g, 0.041 mole) was converted to title product, 3.73 g, m.p. 116°-118°.

Sources & evidence

ORD record
ord-9d2c70d588414e2db1007232f9d5a22a
Source dataset
uspto-grants-1990_12
Patent number
US04977178

Reaction notes

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