Hydrochloric Acid → O-benzyl-N-(2,4,6-trimethoxy-benzyl)hydroxylamine

HRID 1816544

반응식

HRID 1816544 반응식
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:4]=1[CH:5]=O.[CH2:15]([O:22][NH2:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>ClCCl>[CH2:15]([O:22][NH:23][CH2:5][C:4]1[C:3]([O:2][CH3:1])=[CH:10][C:9]([O:11][CH3:12])=[CH:8][C:7]=1[O:13][CH3:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 700192,4,6-TrimethoxybenzaldehydeHCID 102313O-BenzylhydroxylamineHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 22494979O-benzyl-N-(2,4,6-trimethoxy-benzyl)hydroxylamine수율 83%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2,4,6-Trimethoxybenzaldehyde (12.42 g, 63.3 mmol) and O-benzylhydroxylamine (7.80 g, 63.3 mmol) were stirred in dichloromethane (65 mL) at rt overnight. The solvent was removed under reduced pressure. The crude residue was dissolved in ethanol (550 mL) and sodium cyanoborohydride (12.0 g, 189.9 mmol) was added dropwise. The mixture was stirred for 5-10 min, then 12 N HCl was added dropwise until pH became below 3. The reaction mixture was stirred for additional 3 h and 1 N NaOH was added until pH>8. The product was extracted with dichloromethane. The organic phase was dried over Na2SO4 and concentrated under vacuo. The residue was purified by flash chromatography (5% ether in dichloromethane) to give 15.9 g of O-benzyl-N-(2,4,6-trimethoxy-benzyl)hydroxylamine as an oil (83% yield).

후처리

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe crude residue was dissolved in ethanol (550 mL)
  3. stirringThe reaction mixture was stirred for additional 3 h
  4. extractionThe product was extracted with dichloromethane
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated under vacuo
  7. customThe residue was purified by flash chromatography (5% ether in dichloromethane)

출처 및 근거

ORD 기록
ord-c82029e8226e4b60aef08c7dc6342d43
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06884907B2

연결된 노트

불러오는 중…