1,2-Hydrazinedicarboxaldehyde → methyl 2-methoxy-5-(4H-triazol-1-yl)benzoate

HRID 323450Notes

Reaction equation

HRID 323450 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[CH:14]([NH:16][NH:17]C=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:34](=O)(O)[O-].[Na+]>CO.ClCCl.C(OCC)(=O)C.ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:34][CH2:14][N:16]=[N:17]2)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 123421,2-HydrazinedicarboxaldehydeHCID 14812Phosphorus oxide (P4O10)HCID 89843Methyl 5-amino-o-anisateHCID 516892Sodium Bicarbonate

Product 1

HCID 22009369methyl 2-methoxy-5-(4H-triazol-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 21226129Dichloromethane methanolSolventHCID 21226138Dichloromethane ethylacetateSolvent

Conditions

Temperature
160 °C

Procedure

Alternately, according to the method of J. Med. Chem., 21, 1100 (1978), combine methyl 2-methoxy-5-aminobenzoate (1.8 g, 10 mmol), diformyl hydrazine (0.97 g, 11 mmol), and phosphorous pentoxide (1.84 g, 13 mmol). Heat to 160° C. After 1.5 hours, cool the reaction mixture and add a saturated aqueous solution of sodium bicarbonate. Extract three times with dichloromethane. Dry the combined organic layers over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 40% ethyl acetate/dichloromethane and then 5% methanol/dichloromethane to give methyl 2-methoxy-5-(4H-triazol-1-yl)benzoate: mp; 179-182° C.

Workup

  1. temperaturecool the reaction mixture
  2. extractionExtract three times with dichloromethane
  3. dry with materialDry the combined organic layers over MgSO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customto give a residue

Sources & evidence

ORD record
ord-51d4e5ada01148b294c4f63a0dbc22fa
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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