Hydrochloric Acid → HCID 13220401, compound

HRID 2351882Notes

Reaction equation

HRID 2351882 reaction equation
C(OC([C:6]1[O:17][C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]([CH3:18])[C:8]=2[C:7]=1[OH:19])=O)C.[OH-].[Na+].Cl>C(O)C>[CH3:18][N:9]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[C:16]2[O:17][CH2:6][C:7](=[O:19])[C:8]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54696101Ethyl 3-hydroxy-4-methyl-4H-furo[3,2-b]indole-2-carboxylate

Product 1

HCID 13220401HCID 13220401, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 47.0 g (0.18 mole) of 3-hydroxy-4-methyl-4H-furo[3,2-b]indole-2-carboxylic ethyl ester (Prep. described in U.S. patent application Ser. No. 369,448) in 450 ml of 95% ethanol was treated with 450 ml of 30% aqueous sodium hydroxide. The mixture was stirred at reflux for two hours, cooled, added to 3.0 kg ice/water, and acidified with 6.0 N hydrochloric acid. The product was filtered, washed with water, and recrystallized from ethanol-water to yield 17.9 g (53% yield) of the product, mp 113°-116° C. An additional recrystallization as above raised the mp to 115.5°-118° C.

Workup

  1. temperatureat reflux for two hours
  2. temperaturecooled
  3. filtrationThe product was filtered
  4. washwashed with water
  5. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-769cd07bb5c44cfca8f1c5b599256389
Source dataset
uspto-grants-1989_10
Patent number
US04874758

Reaction notes

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