8-Bromo-3-nitrochroman → 8-Bromo-3,4-dihydro-2H-1-benzopyran-3-amine

HRID 1464699

반응식

HRID 1464699 반응식
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH:8]([N+:12]([O-])=O)[CH2:7]2>C(O)(=O)C.[Zn]>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH:8]([NH2:12])[CH2:7]2

참가 물질

4

반응물 1

HCID 190871628-Bromo-3-nitrochroman

생성물 1

HCID 162444248-Bromo-3,4-dihydro-2H-1-benzopyran-3-amine수율 61%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

8-Bromo-3-nitrochroman (400 mg; 1.55 mmol) was dissolved in glacial acetic acid (30 ml) and zinc dust (2 g) was added. The mixture was heated to 100° C. for 15 minutes. The zinc dust was filtered off and washed with dichloromethane. The solvent was evaporated and the remaining oil extracted with diluted hydrochloric acid/dichloromethane. The phases were separated and the pH of the water layer was adjusted to 11 with 2N NaOH. The water layer was extracted with dichloro-methane. The phases were separated and the organic layer dried (Na2SO4). The solvent was evaporated yielding 214 mg (61%) of 8-bromo-3-aminochroman.

후처리

  1. filtrationThe zinc dust was filtered off
  2. washwashed with dichloromethane
  3. customThe solvent was evaporated
  4. extractionthe remaining oil extracted with diluted hydrochloric acid/dichloromethane
  5. customThe phases were separated
  6. extractionThe water layer was extracted with dichloro-methane
  7. customThe phases were separated
  8. dry with materialthe organic layer dried (Na2SO4)
  9. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-191527e5ddd549eb8ffb5c0415348af8
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05306830

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