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Water → 6-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(4-hydroxybutyl)-1-pyridinyl}-2H-benzo[b]pyran

HRID 487655
Notes
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Reaction equation

HRID 487655 reaction equation
[C:1]([C:3]1[CH:35]=[CH:34][C:6]2[O:7][C:8]([CH3:33])([CH3:32])[CH:9]=[C:10]([N:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][O:21]CC4C=CC(OC)=CC=4)=[CH:13][C:12]3=[O:31])[C:5]=2[CH:4]=1)#[N:2].O.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(Cl)Cl>[C:1]([C:3]1[CH:35]=[CH:34][C:6]2[O:7][C:8]([CH3:32])([CH3:33])[CH:9]=[C:10]([N:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:13][C:12]3=[O:31])[C:5]=2[CH:4]=1)#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962Water2×HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 190925536-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(4-p-methoxybenzyloxybutyl)-1pyridinyl-}-2H-benzo[b]pyran

Product 1

HCID 190925116-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(4-hydroxybutyl)-1-pyridinyl}-2H-benzo[b]pyranYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

In 24 ml of methylene chloride, is dissolved 1.13 g of 6-cyano-2,2-dimethyl-4-{2-oxo-4-(4-p-methoxybenzyloxybutyl)-1-pyridinyl}-2H-benzo[b]pyran obtained in Example 46. Then, 1.33 ml of water is added. Then, 0.82 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone is added at room temperature and the resulting mixture is reacted at that temperature for 40 minutes. After stopping the reaction by adding water, the reaction mixture is extracted with methylene chloride. The organic layer is washed successively with 0.1M aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The inorganic matter is filtered off and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography using 1/10 mixture of methanol/methylene chloride as a developing solvent. Thus, 0.78 g of 6-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(4-hydroxybutyl)-1-pyridinyl}-2H-benzo[b]pyran is obtained.

Workup

  1. customthe resulting mixture is reacted at that temperature for 40 minutes
  2. customthe reaction
  3. extractionthe reaction mixture is extracted with methylene chloride
  4. washThe organic layer is washed successively with 0.1M aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe inorganic matter is filtered off
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography
  9. addition1/10 mixture of methanol/methylene chloride as a developing solvent

Sources & evidence

ORD record
ord-0a795e29ff6b4540b68452b54675e12e
Source dataset
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05296492

Reaction notes

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