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

HRID 1920673Notes

Reaction equation

HRID 1920673 reaction equation
[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

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 25228376HCID 25228376, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-b76f742148f44fabbc5dc630079fb921
Source dataset
uspto-grants-2012_05
Patent number
US08173620B2

Reaction notes

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