Methanol → HCID 22594308, compound

HRID 1761030Notes

Reaction equation

HRID 1761030 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O)#[N:16].[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.CO>ClCCCl>[N:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[NH:25][CH2:20][C:19]1[CH:18]=[C:17]([CH:24]=[CH:23][CH:22]=1)[C:15]#[N:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 104392-AminopyridineHCID 90670m-FormylbenzonitrileHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22594308HCID 22594308, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (23 g; 108 mmol) is added in small portions to a solution, stirred under an argon atmosphere, of 3-cyanobenzaldehyde (10 g; 63.7 mmol) and 2-aminopyridine (6 g; 63.7 mmol) in 300 ml of 1,2-dichloroethane. After stirring for 12 hours at ambient temperature, the reaction mixture is hydrolysed with methanol and concentrated. The residue obtained is purified by chromotography on silica gel (eluant petroleum ether/ethyl acetate, 3/1 then 2/1 and 1/1) to yield the expected product.

Workup

  1. concentrationconcentrated
  2. customThe residue obtained
  3. customis purified by chromotography on silica gel (eluant petroleum ether/ethyl acetate, 3/1

Sources & evidence

ORD record
ord-2fcb83f9b37f4f59ac1d697473b092a4
Source dataset
uspto-grants-2005_01
Patent number
US06846833B2

Reaction notes

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