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Potassium Carbonate → N4-[3-(2-methyl-[1,3]dioxolan-2-yl)propyl]quinoline-3,4-diamine

HRID 521277
ノート
印刷プレビュー

反応式

HRID 521277 の反応式
[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][C:12]=2[N+:21]([O-])=O)[O:6][CH2:5][CH2:4][O:3]1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl.O.CC[N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1.[Br-].[Br-]>[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][C:12]=2[NH2:21])[O:3][CH2:4][CH2:5][O:6]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 69506985[3-(2-Methyl-[1,3]dioxolan-2-yl)propyl](3-nitro-quinolin-4-yl)amine

生成物 1

HCID 86052449N4-[3-(2-methyl-[1,3]dioxolan-2-yl)propyl]quinoline-3,4-diamine収率 97.3%

試薬・触媒・溶媒 3

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromide
触媒
HCID 962Water溶媒
HCID 6344Dichloromethane溶媒

実験手順

The product from the previous step, [3-(2-methyl-[1,3]dioxolan-2-yl)propyl](3-nitro-quinolin-4-yl)amine (29.5 g, 93.0 mmol), was stirred with sodium dithionite (67.0 g, approximately 85% pure), potassium carbonate (51.4 g, 372 mmol), and ethyl viologen dibromide (0.37 g, 1 mmol) in a mixture of dichloromethane and water (375 mL each) for 15 hours. The layers were then separated, and the organic phase was washed successively with a saturated aqueous sodium bicarbonate solution and water (250 mL each), dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide N4-[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]quinoline-3,4-diamine (26.0 g) as a dark solid that was used directly in the next step without further purification.

後処理

  1. customThe layers were then separated
  2. washthe organic phase was washed successively with a saturated aqueous sodium bicarbonate solution and water (250 mL each)
  3. dry with materialdried over potassium carbonate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-dcf6168aac164fa1b1fa7425e09cf23b
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09328110B2

反応ノート

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