Sodium Formate → alpha-Hydroxy-2-nitro-p-tolunitrile

HRID 1250835Notes

Reaction equation

HRID 1250835 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].C([O-])=[O:15].[Na+]>C(O)C.O.C(Cl)Cl.CCOC(C)=O>[OH:15][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 2

HCID 2723810Sodium FormateHCID 219055094-(Bromomethyl)-3-nitrobenzonitrile

Product 1

HCID 17794060alpha-Hydroxy-2-nitro-p-tolunitrileYield 77%

Reagents, catalysts & solvents 2

HCID 19096565Water ethanolSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

A stirred solution containing α-bromo-2-nitro-p-tolunitrile (1.228 g, 5.095 mmol) and sodium formate (0.8664 g, 12.74 mmol) in ethanol:water (4:1, 25 mL) was refluxed for 2 h. The reaction was cooled to room temperature, diluted with 20% CH2Cl2/EtOAc, washed with H2O (3×), dried (MgSO4) and concentrated. Purification by flash chromatography (1,2 and 3% MeOH/CHCl3 gradient) gave 0.695 g (77%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ4.71 (d, 2 H), 5.75 (t, 1 H), 7.89 (dd, J=7.9 Hz, 1 H), 8.14 (d, J=7.9 Hz, 1 H), 8.32 (s, 1 H).

Workup

  1. temperaturewas refluxed for 2 h
  2. washwashed with H2O (3×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification by flash chromatography (1,2 and 3% MeOH/CHCl3 gradient)

Sources & evidence

ORD record
ord-c52194b247734cdd993804d393663dec
Source dataset
uspto-grants-2002_01
Patent number
US06340670B1

Reaction notes

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