Hexanoyl chloride → N-(6-bromo-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)hexanamide

HRID 1506489노트

반응식

HRID 1506489 반응식
Cl.[NH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Br:13])[CH:9]=2)[C:4]1=[O:14].C(N(C(C)C)CC)(C)C.[C:24](Cl)(=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>ClCCl>[Br:13][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4](=[O:14])[CH:3]([NH:2][C:24](=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:12][CH2:11]2

참가 물질

5

반응물 3

HCID 67340Hexanoyl chlorideHCID 81531DiisopropylethylamineHCID 671707672-amino-6-bromo-3,4-dihydronaphthalen-1(2H)-one hydrochloride

생성물 1

HCID 67168280N-(6-bromo-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)hexanamide수율 89.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 2-amino-6-bromo-3,4-dihydronaphthalen-1(2H)-one hydrochloride (Preparation 82B, 1.1 g, 3.98 mmol) in dichloromethane (5 mL) was added diisopropylethylamine (1.737 mL, 9.94 mmol) at 0° C. under a nitrogen atmosphere. To the homogenous solution was added hexanoyl chloride (0.602 mL, 4.38 mmol) dropwise over a period of 3 min. The reaction mixture was allowed to come to room temperature (˜5 min.) and was stirred at room temperature for 3 h. The reaction mixture was partitioned between dichloromethane (30 mL) and 1N HCl (10 mL). The dichloromethane layer was separated, washed with sat. aq. NaHCO3 (20 mL), dried over sodium sulfate and concentrated to yield N-(6-bromo-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)hexanamide (1.2 g, 3.55 mmol, 89% yield) as an off-white solid. LC/MS M+1 339.

후처리

  1. customto come to room temperature
  2. custom(˜5 min.)
  3. customThe reaction mixture was partitioned between dichloromethane (30 mL) and 1N HCl (10 mL)
  4. customThe dichloromethane layer was separated
  5. washwashed with sat. aq. NaHCO3 (20 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-abdadf7a34ba42dbaf6213f6d46bf2ad
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216972B2

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