Hydrochloric Acid → HCID 12764254, compound

HRID 1262920Notes

Reaction equation

HRID 1262920 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-a6b0d46372354670b6977070c2e6a848
Source dataset
uspto-grants-1984_06
Patent number
US04454291

Reaction notes

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