Dichloromethane → HCID 44227675, compound

Reaction equation

[CH3:1][O:2][C:3]1[N:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:4]=1C=O.[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13].[Cl-].[Ca+2].[Cl-].[CH2:20](Cl)Cl>>[C:12]([N:16]=[CH:20][C:8]1[CH:9]=[N:10][C:3]([O:2][CH3:1])=[CH:4][C:7]=1[CH3:11])([CH3:15])([CH3:14])[CH3:13]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 6385Tert-Butylamine

HCID 5284359Calcium Chloride

HCID 144935423-Pyridinecarboxaldehyde, 2-methoxy-4-methyl- (9CI)

Product 1

HCID 44227675HCID 44227675, compoundYield 89%

Procedure

2-Methoxy-4-methylnicotinaldehyde (1.8 g, 12 mmol), tert-butylamine (15 mL), 3 Å molecular sieves (8 g) and dry DCM (10 mL) were mixed and allowed to stand at RT under protection from moisture (calcium chloride tube). After two days the mixture was filtered and the molecular sieves were washed several times with dry DCM. The combined washings were concentrated to give 2.2 g (89%) of the title compound as a crude oil that was used immediately in the next step.