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Ammonium Chloride → 6-(2-Hydroxyphenyl)-5-[(pyrrolidin-1-yl)carbonyl]-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 909319
ノート
印刷プレビュー

反応式

HRID 909319 の反応式
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])CCC.[CH3:11][C:12]1([CH3:32])[CH:29]=[C:28]([CH3:30])[C:27]2[C:14](=[CH:15][CH:16]=[C:17]3[C:26]=2[C:25](=[O:31])[O:24][C:23]2[C:18]3=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:13]1.[NH4+].[Cl-]>O1CCCC1.C(OCC)(=O)C.CCCCCC>[OH:24][C:23]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:17]1[C:26]([C:25]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:31])=[C:27]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([CH3:11])([CH3:32])[CH:29]=[C:28]2[CH3:30]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 31268PyrrolidineHCID 104937872,2,4-Trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-oneHCID 178418339Butyllithium

生成物 1

HCID 580269346-(2-Hydroxyphenyl)-5-[(pyrrolidin-1-yl)carbonyl]-2,2,4-trimethyl-1,2-dihydroquinoline収率 82%

試薬・触媒・溶媒 3

HCID 8028
Tetrahydrofuran
溶媒
2 回
HCID 8058Hexane溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

Pyrrolidine (135 μL, 1.62 mmol) was dissolved in anhydrous tetrahydrofuran (1 mL), and 1.6 M hexane solution of n-butyl litium was added dropwise thereto at 0° C. After the reaction mixture was stirred at same temperature for 30 minutes, an anhydrous tetrahydrofuran solution (3 mL) of 2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one (Reference Compound No. 1-1, 80 mg, 0.27 mmol) was dropped and then the reaction mixture was stirred for 30 minutes more. After the saturated aqueous NH4Cl solution (5 mL) was added to the reaction mixture, the reaction mixture was diluted with ethyl acetate (100 mL). The whole was washed with water (100 mL) and saturated brine (50 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (80.2 mg) as a pale yellow solid. (Yield 82%)

後処理

  1. customat 0° C
  2. addition1-1, 80 mg, 0.27 mmol) was dropped
  3. stirringthe reaction mixture was stirred for 30 minutes more
  4. washThe whole was washed with water (100 mL) and saturated brine (50 mL) successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-c8c296d2f6b34849bc792e0ffda64752
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08017775B2

反応ノート

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