Ammonia → 2-Methylquinolin-7-amine

HRID 882077ノート

反応式

HRID 882077 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=N2)=[CH:4][CH:3]=1.N1CCC[C@H:13]1C(O)=O.C([O-])([O-])=O.[K+].[K+].[NH3:26].[NH4+:27].[Cl-]>CS(C)=O.[Cu](I)I.ClCCl>[CH3:13][C:8]1[CH:7]=[CH:6][C:5]2[C:4](=[CH:3][C:2]([NH2:27])=[CH:11][CH:10]=2)[N:26]=1

参加物

9

反応物 5

HCID 222AmmoniaHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 145742L-ProlineHCID 5212597-Bromoquinoline

生成物 1

HCID 4596552-Methylquinolin-7-amine収率 90%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

The 7-bromoquinoline derivative (800 mg, 3.6 mmol, 1 eq), copper iodide (137 mg, 0.7 mmol, 20 mol %), L-proline (166 mg, 1.4 mmol, 40 mol %) and K2CO3 (1.5 g, 11 mmol, 3 eq) were dissolved in DMSO (20 mL). Aqueous ammonia 28% NH4OH (2 mL) was then introduced and the mixture was heated at 80° C. for 18 hours. After cooling to room temperature, dichloromethane was added followed by a saturated NH4Cl solution. The aqueous layer was extracted twice with dichloromethane, and the combined organic layers were washed again with a saturated NH4Cl solution. The product was purified by column chromatography (SiO2, Cyclohexane-AcOEt 1/3) and obtained as a white powder (511 mg, 90%).

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous layer was extracted twice with dichloromethane
  3. washthe combined organic layers were washed again with a saturated NH4Cl solution
  4. customThe product was purified by column chromatography (SiO2, Cyclohexane-AcOEt 1/3)

出典と根拠

ORDレコード
ord-14273321aae340a296d4dab4e0975e2a
出典データセット
uspto-grants-2015_03
特許番号
US08993767B2

反応ノート

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