Sodium Hydroxide → HCID 13672741, compound

HRID 543038Notes

Reaction equation

HRID 543038 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:9]1[N:14]=[C:13]([CH:15]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][CH:10]=1)#[N:8].[OH-].[Na+].[H][H]>CCOCC.O>[NH2:8][CH2:7][C:9]1[N:14]=[C:13]([CH:15]([O:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 13672735HCID 13672735, compoundHCID 21226445Aluminium lithium hydride2×HCID 178418361HCID 178418361, compound

Product 1

HCID 13672741HCID 13672741, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 0.81 g of 95 percent lithium aluminum hydride in 25 ml of ether was slowly added a solution of 5.90 g of 6-cyano-2-(diphenoxymethyl)pyridine in 60 ml of ether so as to maintain a gentle reflux. The mixture was allowed to stir for about 4 hours. An additional 0.2-0.3 g of lithium aluminum hydride was added. Since no additional reaction occurred, 5 ml of water, 5 ml of 15 percent sodium hydroxide and 20 ml of water were added consecutively. The reaction mixture was filtered and the organic portion separated. The aqueous portion was washed with ether and the combined organic portions were dried over magnesium sulfate. The solvent was stripped off and the residue was dissolved in methylene chloride and then diluted with ~900 ml of hexane. The solution was passed through a silica gel column and the silica gel was rinsed with methylene chloride and then with methanol. The methanol was stripped off leaving the above named product in a yield of 3.0 grams. The structure of the product was confirmed by its NMR and IR Spectrum. Upon analysis, the product was found to have carbon, hydrogen and nitrogen contents of 72.44, 5.92 and 8.82 apercent, respectively as compared with the theoretical contents of 74.51, 5.88 and 9.15 percent, respectively as calculated for the above named compound (Compound 30).

Workup

  1. temperatureto maintain a gentle reflux
  2. customSince no additional reaction
  3. filtrationThe reaction mixture was filtered
  4. customthe organic portion separated
  5. washThe aqueous portion was washed with ether
  6. dry with materialthe combined organic portions were dried over magnesium sulfate
  7. dissolutionthe residue was dissolved in methylene chloride
  8. additiondiluted with ~900 ml of hexane
  9. washthe silica gel was rinsed with methylene chloride
  10. customleaving the above named product in a yield of 3.0 grams

Sources & evidence

ORD record
ord-e5850a3e1957491b93cdd3874a35418d
Source dataset
uspto-grants-1987_04
Patent number
US04661144

Reaction notes

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