Butanal → HCID 86746659, compound

HRID 2399754Notes

Reaction equation

HRID 2399754 reaction equation
[C:1]([NH:7][NH2:8])(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].S([O-])([O-])(=O)=O.[Mg+2].[CH:15](=O)[CH2:16][CH2:17]C.[BH4-].[Na+].Cl[CH2:23]Cl>C(O)C>[N:7]#[N:8].[CH2:3]([CH:2]([CH2:15][CH2:16][CH3:17])[C:1]([NH:7][NH2:8])=[O:6])[CH2:4][CH2:5][CH3:23]

Participants

7

Reactant 5

HCID 261ButanalHCID 6344DichloromethaneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 93202ValerohydrazideHCID 4311764Sodium borohydride

Product 1

HCID 86746659HCID 86746659, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 400 g (3.44 mol) of valeric acid hydrazide (Lancaster Synthesis) in 3000 mL of dichloromethane under a nitrogen atmosphere, was added 250 g (2 mol) of anhydrous magnesium sulfate and 310 g (3.88 mol) of butyraldehyde. The reaction was stirred at ambient temperature for 17 h, filtered, and concentrated in vacuo providing 613 g of nearly colorless solid: mp 66.5°-68.0° C.; NMR (CDCl3) δ 0.97 (t, J=7Hz, 3H), 0.92 (t, J=7Hz, 3H), 1.31-1.46 (m, 2H), 1.48-1.73 (m, 4H), 2.19-2.28 (m, 2H), 2.62 (t, J=7Hz, 2H), 7.14 (t, J=6Hz, 1H), 9.18 (br s, 1H). This material was dissolved in 3000 mL of ethanol and cooled to 0° C. in an ice bath prior to the addition of 130.1 g (3.44 mol) of sodium borohydride. The reaction was maintained at 0° C. for 3 h and then allowd to slowly warm to ambient temperature overnight. The volatiles were removed in vacuo and the residue dissolved in 1500 mL of water and conninuousiy extracted with ether/dichloromethane (1:1) overnight. The extracts were dried (Na2SO4) and concentrated in vacuo to give 549 g (93%) of colorless N2 -butyl valeric acid hydrazide: mp 66.0°-67.5° C.; NMR (CDCl3) δ0.92 (t, J=7Hz, 6H), 1.17-1.52 (m, 6H), 1.56-1.69 (m, 2H), 2.14 (t, J=7Hz, 2H), 2.82 (t, J=7Hz, 2H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customproviding 613 g of nearly colorless solid
  4. temperaturecooled to 0° C. in an ice bath
  5. temperatureThe reaction was maintained at 0° C. for 3 h
  6. temperatureto slowly warm to ambient temperature overnight
  7. customThe volatiles were removed in vacuo
  8. dissolutionthe residue dissolved in 1500 mL of water
  9. extractionconninuousiy extracted with ether/dichloromethane (1:1) overnight
  10. dry with materialThe extracts were dried (Na2SO4)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-65e21945dc484824a750585ee648866f
Source dataset
uspto-grants-1995_09
Patent number
US05451591

Reaction notes

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