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

HRID 598387

반응식

HRID 598387 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromide촉매HCID 962Water용매3회HCID 6344Dichloromethane용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-b5ae80c3c6144dd9ba51534717919eef
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897597B2

연결된 노트

불러오는 중…