Hydrochloric Acid → 6-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 32079노트

반응식

HRID 32079 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=[N:12]O)[CH2:6][CH2:5]2.Cl.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([NH2:12])[CH2:6][CH2:5]2

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 734461306-bromo-3,4-dihydro-1H-naphthalen-2-one Oxime

생성물 1

HCID 100595666-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of BH3-THF complex (1M) (35.9 mL, 35.9 mmol) was added drop-wise to a stirred solution of 6-bromo-3,4-dihydro-1H-naphthalen-2-one oxime (Step A) (3.450 g, 14.37 mmol) in THF (125 ml) at 0° C. The mixture was warmed to RT and to reflux for 24 h. The reaction was cooled to RT and 1 N aqueous HCl was added carefully until the mixture was acidic and the system was stirred until no further gas was evolved. The solution was made basic by the addition of NaOH and the aqueous layer was extracted with EtOAc. The combined organics were dried over MgSO4 and concentrated in vacuo to afford the crude title compound, which was purified by flash column chromatography to yield the title compound. MS (APCI pos) 228 (M+H).

후처리

  1. temperatureto reflux for 24 h
  2. temperatureThe reaction was cooled to RT
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organics were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto afford the crude title compound, which
  7. customwas purified by flash column chromatography

출처 및 근거

ORD 기록
ord-3c302a1131744702a5086e89cb68d9fa
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425631B2

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