Water → HCID 54443150, compound

HRID 1531984Notes

Reaction equation

HRID 1531984 reaction equation
[CH2:1]([N:9]1[C:17]2[C:12](=[C:13]([CH3:30])[C:14]([CH2:26][CH2:27][C:28]#N)=[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-:31].[Na+].[OH2:33]>>[CH2:1]([N:9]1[C:17]2[C:12](=[C:13]([CH3:30])[C:14]([CH2:26][CH2:27][C:28]([OH:33])=[O:31])=[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]

Participants

4

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 54038612HCID 54038612, compound

Product 1

HCID 54443150HCID 54443150, compound

Procedure

N-(1-Octyl-5-cyanoethyl-4,6-dimethylindolin-7-yl)-2,2-dimethyl-propanamide (1.14 g) was dissolved in ETOH (26 ml), and a solution of NaOH (1.1 g) in water (7.5 ml) was added, which was followed by refluxing for 14 hr under a nitrogen atmosphere. EtOH was evaporated under reduced pressure. The obtained residue was dissolved in warm water (30 ml) and washed with AcOEt (30 ml). The aqueous layer was neutralized with 2N HCl and extracted with CHCl3 (50 ml). CHCl3 layer was evaporated under reduced pressure to give 830 mg of the title compound.

Workup

  1. temperatureby refluxing for 14 hr under a nitrogen atmosphere
  2. customEtOH was evaporated under reduced pressure
  3. dissolutionThe obtained residue was dissolved in warm water (30 ml)
  4. washwashed with AcOEt (30 ml)
  5. extractionextracted with CHCl3 (50 ml)
  6. customCHCl3 layer was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8c273f98a4e4412ba8c0474d3599062e
Source dataset
uspto-grants-2001_03
Patent number
US06200988B1

Reaction notes

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