Pyridine → 2-chloro-4-[(E)-hydroxyiminomethyl]-3-methylbenzonitrile

HRID 872816Notes

Reaction equation

HRID 872816 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([CH:11]=O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].N1C=CC=CC=1.Cl.[NH2:20][OH:21]>C1COCC1>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8](/[CH:11]=[N:20]/[OH:21])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 872947742-Chloro-4-formyl-3-methylbenzonitrile

Product 1

HCID 872947342-chloro-4-[(E)-hydroxyiminomethyl]-3-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

2-chloro-4-formyl-3-methylbenzonitrile (5.0 g, 27.8 mmol) was dissolved in dry THF (60 ml). Pyridine (6.7 ml, 84.0 mmol) and hydroxylamine hydrochloride (3.87 g, 55.7 mmol) were added to the solution. The mixture was heated to 70° C. and stirred for 4 h. THF was evaporated and ice water (50 ml) was added. The mixture was stirred for 1 h and the precipitate was filtered off and washed twice with cold water. After drying (5.3 g) of the title compound was obtained. 1H-NMR (400 MHz; d6-DMSO): δ 2.48 (s, 3H), 7.79 (m, 2H), 8.45 (s, 1H), 11.93 (s, 1H).

Workup

  1. customTHF was evaporated
  2. additionice water (50 ml) was added
  3. stirringThe mixture was stirred for 1 h
  4. filtrationthe precipitate was filtered off
  5. washwashed twice with cold water
  6. dry with materialAfter drying (5.3 g) of the title compound
  7. customwas obtained

Sources & evidence

ORD record
ord-aabc60167ca640af939d41fadfb4206c
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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