Acetaldehyde → 3-Cyano-2-ethylamino-6-dimethoxymethylpyridine

HRID 368979Notes

Reaction equation

HRID 368979 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[C:4]([CH:10]([O:13][CH3:14])[O:11][CH3:12])[N:3]=1.[CH:15](=O)[CH3:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[C:8]([C:7]1[C:2]([NH:1][CH2:15][CH3:16])=[N:3][C:4]([CH:10]([O:13][CH3:14])[O:11][CH3:12])=[CH:5][CH:6]=1)#[N:9]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 232844912-Amino-3-cyano-6-dimethoxymethylpyridine

Product 1

HCID 232844663-Cyano-2-ethylamino-6-dimethoxymethylpyridineYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Amino-3-cyano-6-dimethoxymethylpyridine (39.6 g, 0.2 mol) and 12 ml (0.2 mol) of acetaldehyde were dissolved in 400 ml of acetic acid, and the resulting solution was mixed with 45.5 g (0.2 mol) of sodium triacetoxyborohydride and stirred for 2.5 hours at room temperature. The reaction solution was concentrated under a reduced pressure, diluted with chloroform and then washed with 1 N sodium hydroxide aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate was removed by filtration and then the filtrate was concentrated under a reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 33.9 g of 3-cyano-2-ethylamino-6-dimethoxymethylpyridine as an oily material. The yield was 77%.

Workup

  1. concentrationThe reaction solution was concentrated under a reduced pressure
  2. additiondiluted with chloroform
  3. washwashed with 1 N sodium hydroxide aqueous solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate
  5. customwas removed by filtration
  6. concentrationthe filtrate was concentrated under a reduced pressure
  7. customThereafter, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-5879856c9a134506b3b09bea45ca9aa3
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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