HCID 13021007, compound → HCID 21103205, compound

HRID 1354801Notes

Reaction equation

HRID 1354801 reaction equation
[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[C:9]([N+:14]([O-])=O)[CH:8]=2)=[N:3]1>CO.CCOC(C)=O.[Ni]>[CH3:1][N:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:8]=[C:9]([NH2:14])[C:10]([NH2:11])=[CH:12][CH:13]=2)[NH:3]1

Participants

4

Reactant 1

HCID 13021007HCID 13021007, compound

Product 1

HCID 21103205HCID 21103205, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

4-(2-Methyl-2H-tetrazol-5-yl)-2-nitroaniline (8-3) (242 mg, 1.1 mmol) in MeOH-EtOAc (1:1, 200 mL) was hydrogenized (H2 pressure 50 psi) in the presence of Raney-Ni (35 mg) overnight. After this time, the reaction solution color was changed from yellow to colorless. LCMS indicated that the starting material was completely disappeared but the product peak was weak. The catalyst was filtered and washed with MeOH (2×20 mL). The collected MeOH-EtOAc solution was concentrated to afford the desired pure product (8-4) (208 mg, 100%) according to 1H NMR. 1H NMR (500 MHz, DMSO-d6): δ7.26 (d, J=2.0 Hz, 1H), 7.12 (dd, J=8.0, 2.0 Hz, 1H), 6.59 (d, J=8.0 Hz, 1H), (s, 2H), 4.93 (s, 2H), 4.72 s, 2H), 4.34 (s, 3H).

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with MeOH (2×20 mL)
  3. concentrationThe collected MeOH-EtOAc solution was concentrated

Sources & evidence

ORD record
ord-120ec171f90d4d02b245a662593326a5
Source dataset
uspto-grants-2007_05
Patent number
US07223738B2

Reaction notes

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