1: 2-picoline With tert.-butyl lithium in tetrahydrofuran T=-78°C; 1 h; Inert atmosphere; 2: allyl bromide in tetrahydrofuran T=-78 - 20°C; Inert atmosphere;

1: With citric acid in methanol T=60°C; pH=4; 2: With sodium hydroxide in methanol T=25°C; pH=12;

1: 2-picoline With n-butyllithium in tetrahydrofuran; toluene T=0 - 5°C; Metallation; 0.5 h; 2: 3-chloroprop-1-ene in tetrahydrofuran; toluene T=0 - 5°C; Alkylation; 0.5 h;

CuCN*2LiCl in tetrahydrofuran T=-60 - 0°C; 6 h; Inert atmosphere;

1.1: pyridine-2-carboxylic acid; copper(l) iodide; caesium carbonate / 1,4-dioxane / 16 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 25 °C 3.1: sodium hydroxide / methanol / 16 h / 25 °C 3.2: pH 4 4.1: citric acid / methanol / 60 °C / pH 4 4.2: 25 °C / pH 12 View Scheme

1.1: sodium hydroxide / methanol / 16 h / 25 °C 1.2: pH 4 2.1: citric acid / methanol / 60 °C / pH 4 2.2: 25 °C / pH 12 View Scheme

1.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 25 °C 2.1: sodium hydroxide / methanol / 16 h / 25 °C 2.2: pH 4 3.1: citric acid / methanol / 60 °C / pH 4 3.2: 25 °C / pH 12 View Scheme