1,1-Dimethoxyethyl(dimethyl)amine → HCID 54494796, compound

HRID 1638449Notes

Reaction equation

HRID 1638449 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][C:11]2=[O:19])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].CO[C:22](OC)([N:24]([CH3:26])[CH3:25])[CH3:23]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[C:22]([N:24]([CH3:26])[CH3:25])[CH3:23])[C:11]2=[O:19])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 13339543HCID 13339543, compound

Product 1

HCID 54494796HCID 54494796, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-(3-Chloro-4-methoxyphenyl)-2(1H,3H)-indolone (0.67 g, 2.45 mmole), dimethylacetamide dimethylacetal (90%, 0.45 ml, 2.7 mmole) and 10 ml CHCl3 were refluxed under nitrogen for 3 hours. The reaction mixture was cooled and evaporated in vacuo to a viscous oil. The oil was column chromatographed on silica gel, eluting impurities with ethyl acetate and then product with 2-4% methanol in ethyl acetate, initially isolated as an oil (793 mg). Crystallization from ether gave purified title product, 625 mg, m.p. 138°-141°.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated in vacuo to a viscous oil
  3. customchromatographed on silica gel
  4. washeluting impurities with ethyl acetate

Sources & evidence

ORD record
ord-1266472c539a4cc29d3192e3a85d7a66
Source dataset
uspto-grants-1989_11
Patent number
US04879391

Reaction notes

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