Hydroxyamine hydrochloride → 3-Cyanophenylboronic acid

HRID 498130Notes

Reaction equation

HRID 498130 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([B:9]([OH:11])[OH:10])[CH:6]=[CH:7][CH:8]=1)=O.Cl.[NH2:13]O.C([O-])=O.[Na+]>C(O)=O>[C:1]([C:3]1[CH:4]=[C:5]([B:9]([OH:11])[OH:10])[CH:6]=[CH:7][CH:8]=1)#[N:13]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium FormateHCID 27343563-Formylphenylboronic acid

Product 1

HCID 27343253-Cyanophenylboronic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

In a three-necked flask with a capacity 3 liters, 123.4 g of the 3-formylphenylboronic acid prepared in Production Example 2, 68.6 g of hydroxylamine hydrochloride, 1050 ml of formic acid and 112.1 g of sodium formate are placed and mixed with each other. The resultant mixture liquid was heated for 8 hours while refluxing. The resultant reaction mixture liquid was left to stand in the ambient atmosphere for one night. Thereafter, in the case where a precipitate was generated in the reaction mixture liquid, this mixture liquid was agitated while cooling with ice and, in the case where no precipitate was generated in the reaction mixture liquid, the mixture liquid was mixed with a small amount of precipitation seed particles and agitated. From the resultant reaction mixture liquid, the solid precipitate was collected, by filtration and dried. The target compound, 3-cyanophenylboronic acid was obtained in an amount of 82.0 g. The yield thereof was 68%. The results of the 1H-NMR measurement of the target compound (200 MHz, δ ppm, CDCl3) were shown below.

Workup

  1. additionmixed with each other
  2. temperaturewhile refluxing
  3. customThe resultant reaction mixture liquid
  4. waitwas left
  5. waitto stand in the ambient atmosphere for one night
  6. temperaturewhile cooling with ice and, in the case where no precipitate
  7. additionthe mixture liquid was mixed with a small amount of precipitation seed particles
  8. stirringagitated
  9. customFrom the resultant reaction mixture liquid
  10. filtrationthe solid precipitate was collected, by filtration
  11. customdried

Sources & evidence

ORD record
ord-b765acd6e7d94a57a75acbcfb536575a
Source dataset
uspto-grants-2005_09
Patent number
US06949668B2

Reaction notes

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