3-Hydroxy-2,2-dimethylpropionaldehyde → 3-(6,7-Dimethoxyquinolin-3-yl-amino)-2,2-dimethyl-propan-1-ol

HRID 1859498Notes

Reaction equation

HRID 1859498 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[C:7]([O:14][CH3:15])[CH:6]=2.[CH3:16][C:17]([CH3:22])([CH2:20]O)[CH:18]=[O:19]>CO>[CH3:13][O:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[O:14][CH3:15])[N:4]=[CH:3][C:2]([NH:1][CH2:16][C:17]([CH3:22])([CH3:20])[CH2:18][OH:19])=[CH:11]2

Participants

4

Reactant 2

HCID 116993-Hydroxy-2,2-dimethylpropionaldehydeHCID 10330538HCID 10330538, compound

Product 1

HCID 225731783-(6,7-Dimethoxyquinolin-3-yl-amino)-2,2-dimethyl-propan-1-olYield 21.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The reaction is run similar to the preparation in Example 11. To a MeOH solution of 4 Å powdered molecular sieves (0.35 g) under argon is added 3-amino-6,7-dimethoxyquinoline (0.32 g , 1.6 mmol) and 2,2-dimethyl-3-hydroxypropionaldehyde (0.19 g, 1.9 mmol). The product mixture is chromatographed (3% MeOH/CHCl3) to afford 0.10 g of material which is partitioned between CH2Cl2/10% NaOH. The organic layer is washed with 10% NaOH, H2O, and brine, then dried (MgSO4), and recrystallized from EtOAc/hexanes to provide a light-orange solid (m.p. 170-173.5° C.). Anal. Calcd. for C16H22N2O3: C, 66.18; H, 7.64; N, 9.65; Found: C, 66.11; H, 7.49; N, 9.33.

Workup

  1. customThe reaction is run similar to the preparation in Example 11
  2. customThe product mixture is chromatographed (3% MeOH/CHCl3)

Sources & evidence

ORD record
ord-a2d6b75cb3dd45d0b05af01099699b36
Source dataset
uspto-grants-2003_03
Patent number
US06528526B1

Reaction notes

Loading…