Water → 1-(4,4-dimethyl-7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanone

HRID 2219980ノート

反応式

HRID 2219980 の反応式
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1.[C:16](OC(=O)C)(=[O:18])[CH3:17].O>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[N:5]([C:16](=[O:18])[CH3:17])[CH2:4][CH2:3]1

参加物

6

反応物 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 219614774,4-Dimethyl-7-nitro-1,2,3,4-tetrahydroquinoline

生成物 1

HCID 590215001-(4,4-dimethyl-7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanone収率 92%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

実験手順

To a stirred solution of 1,2,3,4-tetrahydro-4,4-dimethyl-7-nitroquinoline (Rami et al, WO 03/068749) (500 mg, 2.42 mmol), DMAP (5 mg) in pyridine (2 mL) was added acetic anhydride (0.46 mL, 4.9 mmol). The mixture was stirred at room temperature for 10 h, and then heated at 60° C. for 5 h. After cooling, the mixture was treated with water and extracted with EtOAc. The combined organic layers were washed with sat. aq. NaHCO3, 1N HCl, brine, dried, and evaporated. The residue was purified by chromatography to give a light yellow solid (550 mg, 92%).

後処理

  1. temperatureheated at 60° C. for 5 h
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with sat. aq. NaHCO3, 1N HCl, brine
  5. customdried
  6. customevaporated
  7. customThe residue was purified by chromatography

出典と根拠

ORDレコード
ord-3918ddff1ace42168345f296e94a4cec
出典データセット
uspto-grants-2008_08
特許番号
US07414131B2

反応ノート

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