Hydrochloric Acid → 2'-(1H-Tetrazol-5-yl)-1,1'-biphenyl-4-carboxaldehyde (Losartan Impurity)

HRID 644925Notes

Reaction equation

C([O:3][CH:4](OCC)[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]2[N:18]=[N:19][N:20](C3CCCCO3)[N:21]=2)=[CH:7][CH:6]=1)C.C(O)C.Cl>O>[NH:21]1[C:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:8]2[CH:9]=[CH:10][C:5]([CH:4]=[O:3])=[CH:6][CH:7]=2)=[N:18][N:19]=[N:20]1

Participants

Conditions

Temperature: 45 °C

Procedure

To 5-(4′-diethoxymethyl-biphenyl-2-yl)-2-(tetrahydropyran-2-yl)-2H-tetrazole (0.408 g; 1.00 mmol) are added 94% ethanol (2.5 mL) and a 2N aqueous solution of hydrochloric acid (0.5 mL; 1.0 mmol). The resulting solution is heated to 45° C. for 3 hours. After the addition of water (about 2 mL) the mixture is allowed to cool down to room temperature and then stirred at 0 to 5° C. for 30 minutes. The resulting suspension is filtered and the solids are washed with a small amount of water, dried in vacuo at 40° C. to afford 2′-(1H-tetrazol-5-yl)biphenyl-4-carbaldehyde as white, crystalline powder.

Workup

temperatureto cool down to room temperature
filtrationThe resulting suspension is filtered
washthe solids are washed with a small amount of water
customdried in vacuo at 40° C.

Sources & evidence

ORD record: ord-462ebbd455dc47a788eeacbc2dd370a6
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700784B2

Reaction notes

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