p-Cyanobenzyl alcohol → N-Hydroxy-4-(hydroxymethyl)benzimidamide

HRID 1941874노트

반응식

HRID 1941874 반응식
[OH:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.Cl.[NH2:12][OH:13].C([O-])(O)=O.[Na+]>CO>[OH:13][N:12]=[C:7]([NH2:8])[C:6]1[CH:9]=[CH:10][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=1

참가 물질

5

반응물 3

HCID 160549p-Cyanobenzyl alcoholHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

생성물 1

HCID 53437716N-Hydroxy-4-(hydroxymethyl)benzimidamide수율 101.8%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

A solution of 4-(hydroxymethyl)benzonitrile (22.43 g, 0.1685 g), hydroxylamine hydrochloride (18.67 g, 0.2689 mol) and NaHCO3 (45.22 g, 0.538 mol) in methanol (250 mL) was heated to reflux overnight. Upon cooling, the heterogeneous mixture was filtered and the solids were washed with additional methanol. The filtrate was evaporated to dryness to afford an off-white solid. The solids were suspended in ˜75 mL hot methanol, then cooled to room temperature and filtered. The filtrate was evaporated to afford N′-hydroxy-4-(hydroxymethyl)benzimidamide (28.5 g) as a white solid. The material was used without further purification. The compound had an HPLC retention time=0.232 min. −Column: CHROMOLITH® SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.2% H3PO4; Solvent B=90% MeOH, 10% H2O, 0.2% H3PO4. LC/MS M+1=167.3

후처리

  1. temperatureto reflux overnight
  2. temperatureUpon cooling
  3. filtrationthe heterogeneous mixture was filtered
  4. washthe solids were washed with additional methanol
  5. customThe filtrate was evaporated to dryness
  6. customto afford an off-white solid
  7. filtrationfiltered
  8. customThe filtrate was evaporated

출처 및 근거

ORD 기록
ord-a3bfb01f27d442ed8e07de3525291c7d
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389509B2

반응 노트

불러오는 중…