1-(5-methyl-4-(o-tolyl)-4H-1,2,4-triazol-3-yl)-2-phenylethanone oxime → 1-(5-methyl-4-(o-tolyl)-4H-1,2,4-triazol-3-yl)-2-phenylethanamine

HRID 1506632

Reaction equation

HRID 1506632 reaction equation
[CH3:1][C:2]1[N:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[C:4]([C:7](=[N:15]O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][N:6]=1>C(O)(=O)C.[Zn]>[CH3:1][C:2]1[N:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[C:4]([CH:7]([NH2:15])[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][N:6]=1

Participants

4

Reactant 1

HCID 1366114361-(5-methyl-4-(o-tolyl)-4H-1,2,4-triazol-3-yl)-2-phenylethanone oxime

Product 1

HCID 902815191-(5-methyl-4-(o-tolyl)-4H-1,2,4-triazol-3-yl)-2-phenylethanamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

The suspension of 10E (120 mg, 0.4 mmol) and zinc powder (256 mg, 4 mmol) in 2 mL of acetic acid was heated to reflux for 30 minutes. The reaction was filtered and purified on prep reverse phase HPLC using 20-80% B over 20 min. (A=0.1% TFA/H2O; B=0.1% TFA/Acetonitrile). Combined pure fractions as determined by LC/MS and lyophilized to provide the desired product. MS (m/z) 293 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes
  3. filtrationThe reaction was filtered
  4. custompurified on prep reverse phase
  5. customover 20 min.

Sources & evidence

ORD record
ord-528daa2f527145d6898db0421b15a31c
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Linked notes

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