Methyl (1,8-diethyl-4-oxo-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate → 4-Oxo Etodolac

HRID 1955719Notes

Reaction equation

HRID 1955719 reaction equation
C[O:2][C:3](=[O:23])[CH2:4][C:5]1([CH2:21][CH3:22])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8](=[O:20])[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19]>CO.O>[CH2:21]([C:5]1([CH2:4][C:3]([OH:23])=[O:2])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8](=[O:20])[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19])[CH3:22]

Participants

3

Reactant 1

HCID 11120627Methyl (1,8-diethyl-4-oxo-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate

Product 1

HCID 112665954-Oxo EtodolacYield 93.6%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of the product produced in step B (1.25 g, 3.9 mmol), K2 CO3 (3.5 g, 25.3 mmol) and 60 ml MeOH/H2O 1:1 was refluxed for 3 h. The methanol was evaporated, and the aqueous residue acidified to pH 1 using 6N HCl. The aqueous phase was extracted with EtOAc. The organic phase was washed with water, dried (MgSO4), and evaporated to produce a crude glass which was recrystallized from EtOAc-hexane to afford 1.1 g of the title compound as a solid, m. p. 198°-201° C.

Workup

  1. customThe methanol was evaporated
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washThe organic phase was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto produce a crude glass which
  7. customwas recrystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-c00192f7b2524ef4881fdf06b4db48ed
Source dataset
uspto-grants-1998_07
Patent number
US05776967

Reaction notes

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