Sodium borohydride → 7-(Methoxymethoxy)-8-nitroquinolin-2-yl methanol

HRID 1920673노트

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HRID 1920673 반응식
[BH4-].[Na+].[CH3:3][O:4][CH2:5][O:6][C:7]1[C:16]([N+:17]([O-:19])=[O:18])=[C:15]2[C:10]([CH:11]=[CH:12][C:13]([CH:20]=[O:21])=[N:14]2)=[CH:9][CH:8]=1>CCO.C(Cl)(Cl)Cl>[CH3:3][O:4][CH2:5][O:6][C:7]1[C:16]([N+:17]([O-:19])=[O:18])=[C:15]2[C:10]([CH:11]=[CH:12][C:13]([CH2:20][OH:21])=[N:14]2)=[CH:9][CH:8]=1

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 25228376HCID 25228376, 화합물

생성물 1

HCID 252283787-(Methoxymethoxy)-8-nitroquinolin-2-yl methanol수율 46.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6212Chloroform용매

실험 절차

Referring to FIG. 20, NaBH4 was added to a solution of 9a (18.1 mg, 0.0691 mmol) in absolute EtOH (5 mL). The reaction mixture was stirred for 15 min, diluted with chloroform, washed with water followed by brine. The organic layer was dried over Na2SO4 and the solvent was evaporated to afford 10a (8.3 mg, 0.032 mmol, 45%) as a yellow solid: 1H NMR (CDCl3) δ 8.14 (1H, d, J=8.8 Hz), 7.90 (1H, d, J=9.2 Hz), 7.58 (1H, d, J=9.2 Hz), 7.31 (1H, d, J=8.4 Hz), 5.39 (2H, s), 4.91 (2H, s), 3.54 (3H, s); 13C NMR (CDCl3) δ 162.4, 149.0, 139.1, 136.7, 131.9, 130.6, 123.1, 118.5, 116.3, 95.4, 64.5, 57.1; FTIR (neat) 3583, 2923, 1635, 1516, 1263, 1157, 1084, 1047, 931, 916, 804 cm−1; MS (ESI) m/z calculated for (C12H12N2O5+H)+ 265, found 265; HRMS (ESI) m/z calculated for (C12H12N2O5+H)+ 265.0824, found 265.0814.

후처리

  1. washwashed with water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-b76f742148f44fabbc5dc630079fb921
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173620B2

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