Pyridine → HCID 13770523, compound

HRID 236360Notes

Reaction equation

HRID 236360 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[CH2:5][C:4]1=[O:13])[CH3:2].N1C=CC=CC=1.[Cl:20][CH2:21][C:22](Cl)=[O:23]>ClCCl>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:22](=[O:23])[CH2:21][Cl:20])=[CH:9][CH:10]=2)[CH2:5][C:4]1=[O:13])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 118052822H-Indol-2-one, 1-ethyl-1,3-dihydro-5-hydroxy-

Product 1

HCID 13770523HCID 13770523, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a slurry of 100 g. (0.565 mole) of 1-ethyl-5-hydroxyoxindole in 91.3 ml. (1.13 moles) of pyridine and 565 ml. of dichloromethane at 0° C. was added dropwise a solution of 89.3 ml. (1.13 moles) of chloroacetyl chloride in 100 ml. of dichloromethane. The reaction mixture was allowed to stir for 15 minutes, and was then added to 1 l. of ice cold 2N hydrochloric acid and 500 ml. of dichloromethane. The aqueous layer was extracted once again with 300 ml. of dichloromethane and the combined organic extracts washed once with 500 ml. of a saturated brine solution, dried over magnesium sulfate and concentrated to give the desired product in quantitative yield. A small sample was crystallized from hexane, m.p. 53°-57° C.

Workup

  1. additionwas then added to 1 l
  2. extractionThe aqueous layer was extracted once again with 300 ml
  3. washof dichloromethane and the combined organic extracts washed once with 500 ml
  4. dry with materialof a saturated brine solution, dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7a7450d5e3cd47de85238d877735fac7
Source dataset
uspto-grants-1987_02
Patent number
US04644005

Reaction notes

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