Sodium Thiosulfate → HCID 77174876, compound

HRID 1686076Notes

Reaction equation

HRID 1686076 reaction equation
[CH3:1][N:2]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[C:3]1[C:8]([CH2:9][OH:10])=[CH:7][CH:6]=[CH:5][N:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][N:2]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[C:3]1[N:4]=[CH:5][CH:6]=[CH:7][C:8]=1[CH:9]=[O:10]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 67264764HCID 67264764, compound

Product 1

HCID 77174876HCID 77174876, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {2-[methyl(pyridin-3-yl)amino]pyridin-3-yl}methanol (180 mg) in 8 mL CH2Cl2 was added Dess-Martin periodinane (674 mg). The reaction was stirred at room temperature for 100 min. Saturated aqueous sodium thiosulfate and saturated aqueous sodium bicarbonate were added, and the mixture was stirred vigorously overnight, then partitioned between saturated aqueous sodium bicarbonate and CH2Cl2. The aqueous solution was extracted with CH2Cl2 (2×), and the combined organic solutions were dried (Na2SO4) and concentrated to give 2-[methyl(pyridin-3-yl)amino]nicotinaldehyde in approximately 75% purity. This material was used directly in the next reaction.

Workup

  1. stirringthe mixture was stirred vigorously overnight
  2. custompartitioned between saturated aqueous sodium bicarbonate and CH2Cl2
  3. extractionThe aqueous solution was extracted with CH2Cl2 (2×)
  4. dry with materialthe combined organic solutions were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4fa20ecc17d04fc2b63b4b27a63100ec
Source dataset
uspto-grants-2012_04
Patent number
US08148535B2

Reaction notes

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