Ethyl cyanoacetate → 5'-(2-Cyano-2-ethoxycarbonylvinyl)-1,3,3-trimethylspiro-[indoline-2,3'-[3H]-naphtho[2,1-b][1,4]oxazine]

HRID 376215Notes

Reaction equation

HRID 376215 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[CH:9]([C:11]1[C:20]2[O:21][C:22]3([C:32]([CH3:34])([CH3:33])[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]3[CH3:35])[CH:23]=[N:24][C:19]=2[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)=O>N1CCCCC1.C(O)C>[C:1]([C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:9][C:11]1[C:20]2[O:21][C:22]3([C:32]([CH3:33])([CH3:34])[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]3[CH3:35])[CH:23]=[N:24][C:19]=2[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)#[N:2]

Participants

5

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 153056895'-Formyl-1,3,3-trimethylspiro[indoline-2,3'-[3H]-naphtho[2,1-b][1,4]oxazine]

Product 1

HCID 536585485'-(2-Cyano-2-ethoxycarbonylvinyl)-1,3,3-trimethylspiro-[indoline-2,3'-[3H]-naphtho[2,1-b][1,4]oxazine]

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 0.18 g (1.5 mmol) of ethyl cyanoacetate in a minimum quantity of ethanol are added 0.36 g (1 mmol) of the product of Example 1 and then two drops of piperidine. The mixture is heated at 60° C. until a precipitate appears. The precipitate obtained is filtered off, washed with ethanol and dried.

Workup

  1. customThe precipitate obtained
  2. filtrationis filtered off
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-b382f62596194f3db208fbcf87334264
Source dataset
uspto-grants-2000_02
Patent number
US06019914

Reaction notes

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