Sodium Hydroxide → 4,5-Dihydro-4-oxothiopyrano[3,2-b]indole-5-acetic acid

HRID 918486Notes

Reaction equation

HRID 918486 reaction equation
[O:1]=[C:2]1[C:7]2[N:8]([CH2:15][C:16]([O:18]CC)=[O:17])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:6]=2[S:5][CH:4]=[CH:3]1.[OH-].[Na+]>>[O:1]=[C:2]1[C:7]2[N:8]([CH2:15][C:16]([OH:18])=[O:17])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:6]=2[S:5][CH:4]=[CH:3]1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 20326604Ethyl 4,5-dihydro-4-oxothiopyrano[3,2-b]indole-5-acetate

Product 1

HCID 203266194,5-Dihydro-4-oxothiopyrano[3,2-b]indole-5-acetic acidYield 90%

Conditions

Temperature
95 °C

Procedure

A mixture of 6.0 g (0.021 mole) of ethyl 4,5-dihydro-4-oxothiopyrano[3,2-b]indole-5-acetate and 21 ml of 1N sodium hydroxide solution is stirred for one-half hour at 95°C. The clear solution is cooled, acidified and the solid filtered and recrystallized from isopropanol to give 4.9 g of product, mp 275°-278°C.

Workup

  1. temperatureThe clear solution is cooled
  2. filtrationthe solid filtered
  3. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-75ce4c3a4e664514b53b5efeea20c069
Source dataset
uspto-grants-1976_07
Patent number
US03971806

Reaction notes

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