3-Methylbutanal → HCID 25117585, compound

HRID 2060904Notes

Reaction equation

HRID 2060904 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[C:8]2[O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][CH:15]=1.[CH3:23][CH:24]([CH3:28])[CH2:25][CH:26]=O.[BH4-].[Na+]>CO.O>[CH3:23][CH:24]([CH3:28])[CH2:25][CH2:26][NH:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[C:8]2[O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 115523-MethylbutanalHCID 4311764Sodium borohydrideHCID 59401321HCID 59401321, compound

Product 1

HCID 25117585HCID 25117585, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(8-aminomethylquinolin-4-yloxy)benzamide (23 mg, 0.08 mmol, Preparation 90) in MeOH (5 mL) was added 3-methylbutyraldehyde (8.5 μL, 0.08 mmol) and 4 Å molecular sieves (500 mg). The resulting mixture was heated to 50° C. for 16 h then cooled to rt and NaBH4 (6 mg, 0.16 mmol) was added. After 3 h a few drops of water were added, the mixture filtered and washed with MeOH. Solvent was removed in vacuo and the residue purified by column chromatography (0.25% NH4OH(aq), 5% MeOH in DCM) to give the title compound: RT=2.65 min; m/z (ES+)=364.2 [M+H]+.

Workup

  1. temperaturethen cooled to rt
  2. filtrationthe mixture filtered
  3. washwashed with MeOH
  4. customSolvent was removed in vacuo
  5. customthe residue purified by column chromatography (0.25% NH4OH(aq), 5% MeOH in DCM)

Sources & evidence

ORD record
ord-49ec59d619c145698ae8013a6e392e3e
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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