OC[C:3]1[CH:4]=[C:5]([C:15]#[N:16])[C:6]([C:9]2[CH:14]=[CH:13]C=[CH:11][CH:10]=2)=[CH:7][CH:8]=1.[H-].[Li+].[N-:19]=[N+:20]=[N-:21].C([Al+][CH2:25][CH3:26])C.[Cl-].C([Al+]CC)C.[N-]=[N+]=[N-].[Na+].N([O-])=[O:38].[Na+].[OH-].[Na+].Cl.[N+]([O-])(O)=O>C1(C)C(C)=CC=CC=1.C1(C)C=CC=CC=1>[NH:19]1[C:15]([C:5]2[CH:4]=[CH:3][CH:8]=[CH:7][C:6]=2[C:9]2[CH:14]=[CH:13][C:26]([CH:25]=[O:38])=[CH:11][CH:10]=2)=[N:16][N:21]=[N:20]116.74 g (80 mmol) of the “4-hydroxymethyl-biphenyl-2-carbonitrile” is suspended in 100 ml of dry xylene (isomer mixture) under argon. To this suspension is added at room temperature under stirring 0.636 g (80 mmol) of lithium hydride. The suspension is stirred for an additional 4 hours at 120° C. external temperature and a solution of 160 mmol diethylaluminium azide in toluene (which is prepared separately by stirring 160 mmol of diethylaluminium chloride and 160 mmol of sodium azide in xylene [isomer mixture] at room temperature overnight) is added via syringe. The reaction mixture is heated to reflux (˜120° C.), external temperature ca. 140° C. Conversion is controlled by HPLC analysis. After refluxing for 24 hours the reaction mixture is cooled to room temperature and finally quenched with a solution of 300 mmol of sodium nitrite and of 15% sodium hydroxide (240 mmol). Finally 95 ml of conc. HCl is added under stirring. To the resulting suspension is added at room temperature under stirring 31 g (320 mmol) of 65% nitric acid. The suspension is stirred for an additional 6 hours at 60° C. external temperature (internal Temperature=55° C.). Finally the product is isolated by filtration. The crude 2′-(1H-tetrazol-5-yl)-biphenyl-4-carbaldehyde is obtained.
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