Isopropanol → HCID 14994263, compound

HRID 1084769Notes

Reaction equation

HRID 1084769 reaction equation
[NH2:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:12])([CH3:11])[C:3]1=[O:13].Cl.Cl[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.[CH:22](O)([CH3:24])[CH3:23]>>[CH3:12][C:4]1([CH3:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([N:1]([CH2:23][CH2:22][CH3:24])[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[C:3]1=[O:13]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 818524-Chloropyridine hydrochlorideHCID 15703631HCID 15703631, compound

Product 1

HCID 14994263HCID 14994263, compoundYield 33%

Procedure

To a stirred solution of 1-amino-3,3-dimethyloxindole (7.35 g) and isopropanol (167 ml) was added 4-chloropyridine hydrochloride (8.15 g). The flask was flushed with nitrogen and fitted with a condensor and nitrogen inlet. The reaction mixture was heated at reflux for 9 hours. Upon cooling to room temperature, the reaction mixture was poured into dilute aqueous sodium bicarbonate. The product was extracted thrice with ethyl acetate and once with dichloromethane. The combined organic layers were washed with brine and dried (K2CO3). Filtration and concentration gave the crude product. Purification via flash column chromatography (silica gel, 2% Et3N/0-2% MeOH/ether) afforded 3.5 g (33%) of the desired product.

Workup

  1. customThe flask was flushed with nitrogen
  2. customfitted with a condensor and nitrogen inlet
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 9 hours
  5. additionthe reaction mixture was poured into dilute aqueous sodium bicarbonate
  6. extractionThe product was extracted thrice with ethyl acetate
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried (K2CO3)
  9. filtrationFiltration and concentration
  10. customgave the crude product
  11. customPurification via flash column chromatography (silica gel, 2% Et3N/0-2% MeOH/ether)

Sources & evidence

ORD record
ord-a94a2f8fbe844033ab1cc5fdb8c77b14
Source dataset
uspto-grants-1991_04
Patent number
US05006537

Reaction notes

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