Potassium Carbonate → HCID 86720992, compound

HRID 524934Notes

Reaction equation

HRID 524934 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[N:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[CH3:3].C([O-])([O-])=O.[K+].[K+].Cl[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26]>CN(C=O)C>[CH3:3][N:2]([CH3:1])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[N+:25]([O-:27])=[O:26])=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27357814-Chloro-3-nitropyridineHCID 68176625HCID 68176625, compound

Product 1

HCID 86720992HCID 86720992, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-((dimethylamino)methyl)pyridin-3-ol in DMF (5 mL) was added, K2CO3 (834.8 mg, 6.040 mmol) and the mixture was stirred at RT for 10 min before 4-chloro-3-nitro-pyridine (191.5 mg, 1.208 mmol) was added. The mixture was stirred at RT for 60 h. The reaction mixture was partitioned between EtOAc and NH4Cl aq satd. Combined organic extract was washed with brine, dried (MgSO4) and concentrated in vacuo yielding an oil that purified by SCX column, yielding N,N-dimethyl-1-(5-((3-nitropyridin-4-yl)oxy)pyridin-2-yl)methanamine as a colourless oil. MS (ES+) 275.1.

Workup

  1. additionwas added
  2. customThe reaction mixture was partitioned between EtOAc and NH4Cl aq
  3. extractionCombined organic extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customyielding an oil
  8. customthat purified by SCX column

Sources & evidence

ORD record
ord-8d09fbe67fea4833901bc424ceb97bf2
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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