Hydrochloric Acid → Methyl 4-methyl-3-(2'-oxospiro[cyclopentane-1,3'-indoline]-6'-yl)benzoate

HRID 1619142Notes

Reaction equation

HRID 1619142 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]1[CH:19]=[C:18]2[C:14]([C:15]3([CH2:24][CH2:23][CH2:22][CH2:21]3)[C:16](=[O:20])[NH:17]2)=[CH:13][CH:12]=1.Cl.O1CCOC[CH2:27]1.C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:27])=[O:7])=[CH:4][C:3]=1[C:11]1[CH:19]=[C:18]2[C:14]([C:15]3([CH2:24][CH2:23][CH2:22][CH2:21]3)[C:16](=[O:20])[NH:17]2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 581704674-Methyl-3-(2'-oxospiro[cyclopentane-1,3'-indoline]-6'-yl)benzoic acid

Product 1

HCID 58170465Methyl 4-methyl-3-(2'-oxospiro[cyclopentane-1,3'-indoline]-6'-yl)benzoateYield 91.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 4-methyl-3-(2′-oxospiro[cyclopentane-1,3′-indoline]-6′-yl)benzoic acid (preparation 38, 0.47 g, 1.5 mmol) and a 4M solution of hydrochloric acid in dioxane (2.00 mL, 8.0 mmol) in methanol (2 mL) was heated in a sealed tube at 80° C. with stirring. After stirring overnight the mixture was cooled and ethyl acetate and saturated aqueous potassium carbonate solution were added. The organic layer was washed with brine, dried (MgSO4) and evaporated in vacuo. The resultant oil was taken up in a small amount of ethyl acetate and the suspension was filtered. The filtrate was evaporated to give the title compound (0.46 g, 86%) as a foam.

Workup

  1. stirringAfter stirring overnight the mixture
  2. temperaturewas cooled
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. filtrationthe suspension was filtered
  7. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-7c1796ca1f89425897c040015798e19b
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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