Sodium Hydroxide → HCID 22247323, compound

HRID 1107983Notes

Reaction equation

HRID 1107983 reaction equation
[CH2:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([C:26]([O:28]C)=[O:27])=[C:15]([CH3:25])[C:16]=2[NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[Na+]>CO.O>[CH2:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([C:26]([OH:28])=[O:27])=[C:15]([CH3:25])[C:16]=2[NH:18][C:19](=[O:24])[C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22247353HCID 22247353, compound

Product 1

HCID 22247323HCID 22247323, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

N-(1-Octyl-5-methoxycarbonyl-6-methylindolin-7-yl)-2,2-dimethylpropanamide (580 mg) was dissolved in methanol (10 ml) and a solution of NaOH (290 mg) in water (5 ml) was added, which was followed by stirring at 60° C. for 4 hr. Methanol was evaporated under reduced pressure. Water (50 ml) was added to the residue and the mixture was washed with ethyl acetate (20 ml). The aqueous layer was adjusted to pH 6-7 with 2N sulfuric acid and extracted with chloroform (100 ml). The chloroform layer was washed with water and dried over anhydrous sodium sulfate. Chloroform was evaporated under reduced pressure to give 380 mg of the title compound.

Workup

  1. customMethanol was evaporated under reduced pressure
  2. additionWater (50 ml) was added to the residue
  3. washthe mixture was washed with ethyl acetate (20 ml)
  4. extractionextracted with chloroform (100 ml)
  5. washThe chloroform layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customChloroform was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a2d1e54c78d04054b6db5598b31357ac
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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