Water → 2-[(Isopropylidenamino)oxy]-6-methoxymethoxybenzonitrile

HRID 2351287Notes

Reaction equation

HRID 2351287 reaction equation
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].CC(C)([O-])C.[K+].F[C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][O:23][CH3:24])[C:14]=1[C:15]#[N:16].O>CN(C)C=O>[C:2](=[N:4][O:5][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][O:23][CH3:24])[C:14]=1[C:15]#[N:16])([CH3:3])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 67180Acetone, oximeHCID 148362002-Fluoro-6-methoxymethoxybenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 148362012-[(Isopropylidenamino)oxy]-6-methoxymethoxybenzonitrileYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Acetone oxime (11.14 g, 0.1524 mole) was dissolved in 300 ml of dry dimethyl formamide (DMF) and then potassium t-butoxide (17.0 g, 0.152 mole) was added portionwise. The reaction mixture was allowed to stir for 30 minutes at room temperature and the 2-fluoro-6-methoxymethoxybenzonitrile of Example 1(b) (23.0 g, 0.127 mole) was added in 150 ml of DMF. After 30 minutes the reaction mixture was poured into 1000 ml of water and stirred well as the product crystallized. The product was filtered off, washed well with water, and then taken up in CH2Cl2 and dried with magnesium sulfate. Concentration and recrystallization from methanol-water gave 20.5 g (69%) of 2-[(isopropylideneamino)oxy]-6-methoxymethoxybenzonitrile as fine needles, mp 62°-64° C.

Workup

  1. stirringstirred well as the product
  2. customcrystallized
  3. filtrationThe product was filtered off
  4. washwashed well with water
  5. dry with materialdried with magnesium sulfate
  6. concentrationConcentration and recrystallization from methanol-water

Sources & evidence

ORD record
ord-141d330af809453ba4a036b842182854
Source dataset
uspto-grants-1989_10
Patent number
US04873234

Reaction notes

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