Water → 5'-(2-Cyanovinyl)-1,3,3-trimethylspiro[indoline-2,3'-[3H]-naphtho[2,1-b][1,4]oxazine]

HRID 376211Notes

Reaction equation

HRID 376211 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.[Cl-].[C:31]([CH2:33][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:32].O>ClCCl>[C:31]([CH:33]=[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)#[N:32]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 197040(Cyanomethyl)triphenylphosphonium chlorideHCID 153056895'-Formyl-1,3,3-trimethylspiro[indoline-2,3'-[3H]-naphtho[2,1-b][1,4]oxazine]

Product 1

HCID 536568865'-(2-Cyanovinyl)-1,3,3-trimethylspiro[indoline-2,3'-[3H]-naphtho[2,1-b][1,4]oxazine]

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 ml of a 50% strength sodium hydroxide solution is added to a solution of 0.36 g (1 mmol) of the compound of Example 1 and of 0.34 g (1 mmol) of cyanomethyltriphenylphosphonium chloride in 3 ml of dichloromethane. The mixture is stirred at ambient temperature for 1 hour. 10 ml of water are then added and the aqueous phase is extracted with twice 10 ml of dichloromethane. The organic phase is washed, dried and evaporated. A purification is performed on a silica column (CH2Cl2 eluent).

Workup

  1. extractionthe aqueous phase is extracted with twice 10 ml of dichloromethane
  2. washThe organic phase is washed
  3. customdried
  4. customevaporated
  5. customA purification

Sources & evidence

ORD record
ord-a5f8570637924fefa3ca0013902b2091
Source dataset
uspto-grants-2000_02
Patent number
US06019914

Reaction notes

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