1-Propanol → HCID 24777286, compound

HRID 1467190Notes

Reaction equation

HRID 1467190 reaction equation
[N+]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=1[C:6]#[N:7])([O-])=O.[Na].[CH2:16]([OH:19])[CH2:17][CH3:18]>CN(C=O)C>[N+:12]([C:8]1[CH:9]=[CH:10][CH:11]=[C:4]([O:19][CH2:16][CH2:17][CH3:18])[C:5]=1[C:6]#[N:7])([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 10311-PropanolHCID 520718DinitrobenzonitrileHCID 5360545Sodium

Product 1

HCID 24777286HCID 24777286, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-dinitrobenzonitrile (6 g, 31.07 mmol) in dry DMF (45 mL) at 0° C., was added a solution of sodium (815 mg, 35.42 mmol) in n-propanol (23.5 mL) dropwise over 30 minutes. After compete addition, the reaction mixture was warmed to room temperature and stirred for 2.5 hours. The reaction was poured into an ice/water mixture (250 mL), and the precipitate was collected by filtration and dried to yield 2-nitro-6-propoxybenzonitrile (4.95 g, 77%) as a light brown solid. 1H NMR (400 MHz, CDCl3) δ 1.11 (d, J=7.5 Hz, 3H), 1.93 (sext, J=7.5 Hz, 2H), 4.14 (t, J=7.0 Hz, 2H), 7.31 (d, J=8.6 Hz, 1H), 7.69 (t, J=8.6 Hz, 1H), 7.82 (d, J=8.6 Hz, 1H).

Workup

  1. additionaddition
  2. filtrationthe precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-d8c6831e63784fec8f1069744eb2e4bf
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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