Ammonium Chloride → Tert-butyl 3-amino-4-chlorobenzylcarbamate

HRID 1410195노트

반응식

HRID 1410195 반응식
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][C:3]=1[N+:17]([O-])=O.[NH4+].[Cl-]>[Fe].CCO>[NH2:17][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:2]=1[Cl:1])[CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:11])[CH3:12]

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 22981312tert-Butyl 4-chloro-3-nitrobenzylcarbamate

생성물 1

HCID 22981266Tert-butyl 3-amino-4-chlorobenzylcarbamate

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

A mixture of tert-butyl 4-chloro-3-nitrobenzylcarbamate (crude material from step (b)), Fe powder (17.65 g, 316 mmol), NH4Cl (aq, sat, 100 mL) and EtOH (100 mL) was heated at 90° C. for 4 h and allowed to cool. The pH was adjusted to −10 and the mixture was filtered through Celite. The solids were washed with EtOAc and EtOH and the combined filtrates concentrated to remove the organic solvents. The residue was added to ammonia and the mixture was extracted with DCM. The combined extracts were washed with brine, dried over Na2SO4 and concentrated. Crystallization from EtOAc/petroleum ether gave the sub-title compound. Yield: 15.5 g (75% from 4-chloro-3-nitrobenzylamine).

후처리

  1. temperatureto cool
  2. filtrationthe mixture was filtered through Celite
  3. washThe solids were washed with EtOAc and EtOH
  4. concentrationthe combined filtrates concentrated
  5. customto remove the organic solvents
  6. additionThe residue was added to ammonia
  7. extractionthe mixture was extracted with DCM
  8. washThe combined extracts were washed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. customCrystallization from EtOAc/petroleum ether

출처 및 근거

ORD 기록
ord-67f599a34f7e4cc4b761f03100a27213
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921405B2

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