Hydrochloric Acid → HCID 12764254, compound

HRID 1659304Notes

Reaction equation

HRID 1659304 reaction equation
C([O:3][C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:15][CH3:16])[CH:12]=2)[N:7]1[C:17](=[O:21])[C:18]([CH3:20])=[CH2:19])=[O:5])C.CO.[OH-].[Na+].Cl>[Cl-].[Na+].O.O>[CH3:16][O:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:17](=[O:21])[C:18]([CH3:20])=[CH2:19])[CH:6]([C:4]([OH:5])=[O:3])[CH2:14]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 354078HCID 354078, compound

Product 1

HCID 12764254HCID 12764254, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2,3-dihydro-5-methoxy-1-(2-methyl-1-oxo-2-propenyl)-1H-indole-2-carboxylic acid ethyl ester from Example 23 (8.5 g.) in 45 ml. of reagent-grade methanol was added a solution of 1.32 g. of sodium hydroxide (98% purity) in 16 ml. distilled water with hand swirling. This reaction mixture was stirred at room temperature for 2 hours. With vigorous mechanical stirring, the reaction solution was poured into brine and the slightly turbid mass was acidified with concentrated hydrochloric acid. The resulting mixture was stirred, chilled in an ice-water-salt-bath for one hour and the solids were collected on a sintered-glass funnel and washed twice with cold water, to give 2,3-dihydro-5-methoxy-1-(2-methyl-1-oxo-2-propenyl)-1H-indole-2-carboxylic acid (7.32 g.; m.p. 108°-111°). Recrystallization from ethyl acetate improved the m.p. to 115°-118°.

Workup

  1. stirringThe resulting mixture was stirred
  2. temperaturechilled in an ice-water-salt-bath for one hour
  3. customthe solids were collected on a sintered-glass funnel
  4. washwashed twice with cold water

Sources & evidence

ORD record
ord-6c1bdfbe8d4d4daf97820c368da7fc47
Source dataset
uspto-grants-1981_12
Patent number
US04303583

Reaction notes

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