Sodium Hydroxide → 5'-(2-Cyano-2-p-tolylvinyl)-1,3,3-trimethylspiro-[indoline-2,3'-[3H]-naphtho[2,1-b][1,4]oxazine]

HRID 376214Notes

Reaction equation

HRID 376214 reaction equation
[OH-].[Na+].[CH:3]([C:5]1[C:14]2[O:15][C:16]3([C:26]([CH3:28])([CH3:27])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]3[CH3:29])[CH:17]=[N:18][C:13]=2[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=O.[CH3:30][C:31]1[CH:39]=[CH:38][C:34]([CH2:35][C:36]#[N:37])=[CH:33][CH:32]=1>C1(C)C=CC=CC=1>[C:36]([C:35]([C:34]1[CH:38]=[CH:39][C:31]([CH3:30])=[CH:32][CH:33]=1)=[CH:3][C:5]1[C:14]2[O:15][C:16]3([C:26]([CH3:27])([CH3:28])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]3[CH3:29])[CH:17]=[N:18][C:13]=2[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)#[N:37]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76280p-TolylacetonitrileHCID 153056895'-Formyl-1,3,3-trimethylspiro[indoline-2,3'-[3H]-naphtho[2,1-b][1,4]oxazine]

Product 1

HCID 541697325'-(2-Cyano-2-p-tolylvinyl)-1,3,3-trimethylspiro-[indoline-2,3'-[3H]-naphtho[2,1-b][1,4]oxazine]

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5 ml of a 50% strength sodium hydroxide solution are added to a solution of 0.36 g (1 mmol) of the compound of Example 1, of 0.13 g (1 mmol) of 4-methylbenzyl cyanide and of 0.05 g of polyethylene glycol 400 in 15 ml of toluene. The mixture is left at ambient temperature for 2 hours. The organic phase is separated off, washed with water, dried and evaporated. The product is purified by chromatography on a silica column (CH2Cl2 eluent)

Workup

  1. customThe organic phase is separated off
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. customThe product is purified by chromatography on a silica column (CH2Cl2 eluent)

Sources & evidence

ORD record
ord-840fb67753ad4eedbd8d38d38ca74d8e
Source dataset
uspto-grants-2000_02
Patent number
US06019914

Reaction notes

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