1-Nitropropane → HCID 86718524, compound

HRID 929937Notes

Reaction equation

HRID 929937 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N+:7]([CH2:10][CH2:11][CH3:12])([O-:9])=[O:8].[CH:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1>C1COCC1>[N+:7]([CH:10]([CH2:11][CH3:12])[CH:13]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[OH:20])([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 79031-NitropropaneHCID 103713-PyridinecarboxaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 86718524HCID 86718524, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of LiAlH4 (2M in THF) (0.93 mL, 1.87 mmol) in dry THF (80 mL) at 0° C., was slowly added 1-nitropropane (8.30 mL, 93 mmol) under argon. After 60 min, nicotinaldehyde (2.00 g, 18.7 mmol) was added in one portion. The mixture was stirred for 16 hours, while allowing the temperature to rise from 0° C. to room temperature. The reaction mixture was quenched by addition of 1 mL of 2M aqueous HCl, followed by addition of 4 grams of Na2SO4. The resulting suspension was stirred for 15 minutes and then filtered. The filtrate was concentrated. The residue was purified by column chromatography (40 g SiO2) using EtOAc in hexane from 0% to 100% in order to give the title compound as a white solid (2.6 g, 71%) as a mixture of diastereoisomers A and B. LC-MS: [M+H] 197.1; Rt 0.52 min; (LCMS method 1). A) 1H NMR (400 MHz, CHCl3-d): 8.70-8.60 (m, 2H), 7.80-7.74 (m, 1H), 7.42-7.32 (m, 1H), 5.28 (dd, 1H), 4.70-4.58 (m, 1H), 2.97 (d, 1H), 2.29-2.12 (m, 1H), 1.65-1.42 (m, 1H), 0.99 (t, 3H). B) 1H NMR (400 MHz, CHCl3-d): 8.70-8.60 (m, 2H), 7.80-7.74 (m, 1H), 7.42-7.32 (m, 1H), 5.15 (dd, 1H), 4.70-4.58 (m, 1H), 2.81 (d, 1H), 1.99-1.85 (m, 1H), 1.65-1.42 (m, 1H), 0.94 (t, 3H).

Workup

  1. customat 0° C.
  2. customto rise from 0° C. to room temperature
  3. customThe reaction mixture was quenched by addition of 1 mL of 2M aqueous HCl
  4. additionfollowed by addition of 4 grams of Na2SO4
  5. stirringThe resulting suspension was stirred for 15 minutes
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customThe residue was purified by column chromatography (40 g SiO2)

Sources & evidence

ORD record
ord-cfa12235b0e74c42996b031ac3a7059b
Source dataset
uspto-grants-2016_03
Patent number
US09296733B2

Reaction notes

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