Hydroxyamine hydrochloride → 5-Tert-butyl-2-hydroxyl-3-nitro-benzonitrile

HRID 735798Notes

Reaction equation

HRID 735798 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:14]([O-:16])=[O:15])[C:8]([OH:13])=[C:9]([CH:12]=1)[CH:10]=O)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:18]O.C([O-])=O.[Na+]>C(O)=O.O>[C:1]([C:5]1[CH:6]=[C:7]([N+:14]([O-:16])=[O:15])[C:8]([OH:13])=[C:9]([CH:12]=1)[C:10]#[N:18])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium FormateHCID 7172095HCID 7172095, compound

Product 1

HCID 589806535-Tert-butyl-2-hydroxyl-3-nitro-benzonitrileYield 87.2%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

The above aldehyde (1.4 g, 6.3 mmol), hydroxylamine hydrochloride (0.438 g, 6.3 mmol), and sodium formate (0.771 g, 11.3 mmol) in formic acid (20 mL) were heated overnight, at reflux, then cooled to room temperature. The reaction was diluted with water, and the resulting precipitate was filtered. The solid was taken up in ether, dried over Na2SO4, filtered and concentrated in vacuo to yield 5-tert-butyl-2-hydroxyl-3-nitro-benzonitrile (1.21 g, 87%) as a yellow solid.

Workup

  1. temperatureat reflux
  2. filtrationthe resulting precipitate was filtered
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05b527a5fae147e4a38bce603f896006
Source dataset
uspto-grants-2009_09
Patent number
US07592332B2

Reaction notes

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