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

HRID 1506489ノート

反応式

HRID 1506489 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-abdadf7a34ba42dbaf6213f6d46bf2ad
出典データセット
uspto-grants-2015_12
特許番号
US09216972B2

反応ノート

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