Water → HCID 90411699, compound

HRID 2175961Notes

Reaction equation

HRID 2175961 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[OH-].[K+].[C:11]([O:15][C:16]([N:18]1[CH:22]2[CH2:23][CH2:24][CH:19]1[CH:20]([CH2:25]OS(C)(=O)=O)[CH2:21]2)=[O:17])([CH3:14])([CH3:13])[CH3:12].O>CN(C=O)C>[CH3:1][C:2]1[C:7]([O:8][CH2:25][CH:20]2[CH2:21][CH:22]3[N:18]([C:16]([O:15][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:17])[CH:19]2[CH2:24][CH2:23]3)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 707192-Methylpyridin-3-olHCID 90412152HCID 90412152, compound

Product 1

HCID 90411699HCID 90411699, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-methylpyridin-3-ol in DMF was added KOH. The solution was stirred for 30 min at rt, then the title compound from step A was added and the reaction was heated at 80° C. After 5 h, H2O was added and the mixture extracted with EtOAc. The combined organic layers were dried (MgSO4). Purification via silica gel chromatography (0-7% MeOH in DCM) gave the title compound (201 mg, 90%). MS (ESI) mass calcd. for C18H26N2O3, 318.2; m/z found 319.0 [M+1]+.

Workup

  1. temperaturethe reaction was heated at 80° C
  2. waitAfter 5 h
  3. extractionthe mixture extracted with EtOAc
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. customPurification via silica gel chromatography (0-7% MeOH in DCM)

Sources & evidence

ORD record
ord-47ae68d626144c3098d427316ed97b30
Source dataset
uspto-grants-2015_06
Patent number
US09062078B2

Reaction notes

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