Hydrochloric Acid → HCID 21069888, compound

HRID 348134Notes

Reaction equation

HRID 348134 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]2[N:11]=[N:12][N:13]([CH3:15])[N:14]=2)[CH:3]=1.[ClH:16]>C(O)C.[Pd]>[ClH:16].[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([C:10]2[N:11]=[N:12][N:13]([CH3:15])[N:14]=2)[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 210698874-Fluoro-2-(2-methyl-2H-tetrazol-5-yl)-benzonitrile

Product 1

HCID 21069888HCID 21069888, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of intermediate 58, 4-fluoro-2-(2-methyl-2H-tetrazol-5-yl)-benzonitrile, (330 mg, 1.62 mmol) in ethanol (15 mL) was mixed with 6N HCl (1 mL) and 10% Pd—C (200 mg) under nitrogen. The mixture was then stirred under hydrogen (1 atm) for 3 hrs. After removing the catalyst, the filtrate was concentrated in vacuo to provide 360 mg (Yield 91%) of the title compound as an off-white solid; 1H NMR (500 MHz, DMSO-D6) δ ppm: 4.42 (2H, d, J=2.75 Hz) 4.49 (3H, s) 7.48–7.56 (1m) 7.78 (1H, dd, J=8.7, 5.7 Hz) 7.86 (1H, dd, J=9.8, 2.8 Hz) 8.45 (3H, s); LC/MS m/z 208.

Workup

  1. customAfter removing the catalyst
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2f66294ca8ce44eab8f880f0dec11464
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

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