Indoline → N-(5-hydroxymethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

HRID 1531952Notes

Reaction equation

HRID 1531952 reaction equation
C(OC)#N.N1C2C(=CC=CC=2)CC1.C([N:17]1[C:25]2[C:20](=[C:21]([CH3:39])[C:22]([CH2:34][O:35]C(=O)C)=[C:23]([CH3:33])[C:24]=2[NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:19][CH2:18]1)(=O)C.[OH-].[Na+]>CCO.O>[OH:35][CH2:34][C:22]1[C:21]([CH3:39])=[C:20]2[C:25](=[C:24]([NH:26][C:27](=[O:32])[C:28]([CH3:29])([CH3:30])[CH3:31])[C:23]=1[CH3:33])[NH:17][CH2:18][CH2:19]2

Participants

7

Reactant 4

HCID 10328Indoline2×HCID 14798Sodium HydroxideHCID 137201Cyanic acid, methyl esterHCID 15895573N-(1-acetyl-5-acetoxymethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

Product 1

HCID 15895574N-(5-hydroxymethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamideYield 52.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1.27 (9H, s, —C(CH3)3), 2.04 (3H, s, OCOCH3), 2.23, 2.26, 2.30 (9H, s×3, —CH3×2, >NCOCH3), 3.00 (2H, br, Indoline C3-H), 4.05 (2H, br, Indoline C2—H), 5.20 (2H, s, —CH2O—), 9.10 (1H, br, >NH). (2) N-(1-Acetyl-5-acetoxymethyl-4,6-dimethylindolin-7-yl)-2,2-dimethyl-propanamide (7.5 g) was dissolved in EtOH (70 ml) and a solution of NaOH (8.3 g) in water (20 ml) was added, which was followed by refluxing for 10 hr. EtoH was evaporated under reduced pressure and CHCl3 (200 ml) was added. After washing with water, the mixture was dried over anhydrous sodium sulfate and CHCl3 was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3/MeOH=1/0−10/1) to give 3.0 g of N-(5-hydroxymethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide.

Workup

  1. temperatureby refluxing for 10 hr
  2. customEtoH was evaporated under reduced pressure and CHCl3 (200 ml)
  3. additionwas added
  4. washAfter washing with water
  5. dry with materialthe mixture was dried over anhydrous sodium sulfate and CHCl3
  6. customwas evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: CHCl3/MeOH=1/0−10/1)

Sources & evidence

ORD record
ord-039ba0debce14ec1bccc3a410ff941e9
Source dataset
uspto-grants-2001_03
Patent number
US06200988B1

Reaction notes

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