Sodium Cyanide → N-(1-acetyl-5-cyanomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

HRID 1531957Notes

Reaction equation

HRID 1531957 reaction equation
[C:1](OC)#[N:2].N1C2C(=CC=CC=2)CC1.[C:14]([N:17]1[C:25]2[C:20](=[C:21]([CH3:36])[C:22]([CH2:34]Cl)=[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:16])[CH3:15].[C-]#N.[Na+]>CC#N.C1OCCOCCOCCOCCOCCOC1>[C:14]([N:17]1[C:25]2[C:20](=[C:21]([CH3:36])[C:22]([CH2:34][C:1]#[N:2])=[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:16])[CH3:15]

Participants

7

Reactant 4

HCID 8929Sodium CyanideHCID 10328Indoline2×HCID 137201Cyanic acid, methyl esterHCID 15895572N-(1-Acetyl-5-chloromethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

Product 1

HCID 15524343N-(1-acetyl-5-cyanomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

1.27 (9H, S, C(CH3)3), 2.25 (3H, s, -CH3), 2.30 (6H, s, -CH3, >NCOCH3), 3.00 (2H, br, Indoline C3—H), 4.05 (2H, br, Indoline C2—H), 4.68 (2H, s, -CH2c l), 9.16 (1H, br, >NH). (3) N-(1-Acetyl-5-chloromethyl-4,6-dimethylindolin-7-yl)-2,2-dimethyl-propanamide (21 g) was suspended in CH3CN (150 ml), and NaCN (8.1 g) and 18-crown-6 (870 mg) were added, which was followed by refluxing for 15 hr. CH3CN was evaporated under reduced pressure and CHCl3 (300 ml) was added. The mixture was washed with water and dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure. The obtained residue was washed with boiling MeOH to give 15.5 g of N-(1-acetyl-5-cyanomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide.

Workup

  1. temperatureby refluxing for 15 hr
  2. customCH3CN was evaporated under reduced pressure and CHCl3 (300 ml)
  3. additionwas added
  4. washThe mixture was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customCHCl3 was evaporated under reduced pressure
  7. washThe obtained residue was washed with boiling MeOH

Sources & evidence

ORD record
ord-56054b5cf45e428ca0a22880c95415e0
Source dataset
uspto-grants-2001_03
Patent number
US06200988B1

Reaction notes

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