Potassium Carbonate → 7-benzyloxy-N4-[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]quinoline-3,4-diamine

HRID 598387

反応式

HRID 598387 の反応式
S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH2:15]([O:22][C:23]1[CH:32]=[C:31]2[C:26]([C:27]([NH:36][CH2:37][CH:38]3[CH2:42][O:41][C:40]([CH3:44])([CH3:43])[O:39]3)=[C:28]([N+:33]([O-])=O)[CH:29]=[N:30]2)=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O.ClCCl.CC[N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1.[Br-].[Br-]>[CH2:15]([O:22][C:23]1[CH:32]=[C:31]2[C:26]([C:27]([NH:36][CH2:37][CH:38]3[CH2:42][O:41][C:40]([CH3:44])([CH3:43])[O:39]3)=[C:28]([NH2:33])[CH:29]=[N:30]2)=[CH:25][CH:24]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 67051130(7-Benzyloxy-3-nitro-quinolin-4-yl)[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]amine

生成物 1

HCID 670510967-benzyloxy-N4-[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]quinoline-3,4-diamine収率 100%

試薬・触媒・溶媒 3

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromide触媒HCID 962Water溶媒3 回HCID 6344Dichloromethane溶媒

実験手順

A solution of sodium dithionite (85% pure, 135.07 g, 659.42 mmol) and potassium carbonate (101.27 g, 732.73 mmol) in water (450 mL) was added dropwise to a mechanically stirred mixture of ethyl viologen dibromide (1.1 g, 2.93 mmol) and (7-benzyloxy-3-nitro-quinolin-4-yl)[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]amine (60.0 g, 146.54 mmol) in dichloromethane (500 mL) and water (50 mL). The reaction mixture was stirred at ambient temperature overnight and then diluted with water (600 mL) and stirred for an additional 10 minutes. The organic phase was separated and the aqueous layer was reextracted with dichloromethane (400 mL). The combined organic layers were washed with water (800 mL) and brine (800 mL), dried over sodium sulfate, and concentrated under reduced pressure to afford 55.60 g of 7-benzyloxy-N4-[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]quinoline-3,4-diamine as a brown foam. 1H-NMR (300 MHz, CDCl3) δ 8.38 (s, 1H), 7.83 (d, J=9.3 Hz, 1H), 7.51-7.28 (m, 6H), 7.18 (dd, J=9.2, 2.5 Hz, 1H), 5.16 (s, 2H), 4.35 (br s, 1H), 4.30-4.18 (m, 1H), 4.02 (dd, J=8.3, 6.5 Hz, 1H), 3.81 (br s, 2H), 3.68 (dd, J=8.3, 6.1 Hz, 1H), 3.60-3.46 (m, 1H), 3.40-3.25 (m, 1H), 1.52 (s, 3H), 1.37 (s, 3H); MS (APCI) m/z 380.0 (M+H)+.

後処理

  1. stirringstirred for an additional 10 minutes
  2. customThe organic phase was separated
  3. washThe combined organic layers were washed with water (800 mL) and brine (800 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-b5ae80c3c6144dd9ba51534717919eef
出典データセット
uspto-grants-2011_03
特許番号
US07897597B2

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