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

HRID 2230648Notes

Reaction equation

HRID 2230648 reaction equation
CO[C:3]1[CH:12]=[CH:11][C:10]([NH2:13])=C[C:4]=1[C:5]([O:7][CH3:8])=O.C([NH:16][NH:17]C=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:34](=O)(O)[O-].[Na+].[C:39]([O:42][CH2:43]C)(=[O:41])[CH3:40].ClCCl>CO.ClCCl>[CH3:8][O:7][C:5]1[CH:4]=[CH:3][C:12]([CH:11]2[CH:10]=[N:13][N:17]=[N:16]2)=[CH:34][C:40]=1[C:39]([O:42][CH3:43])=[O:41]

Participants

7

Reactant 5

HCID 123421,2-HydrazinedicarboxaldehydeHCID 14812Phosphorus oxide (P4O10)HCID 89843Methyl 5-amino-o-anisateHCID 516892Sodium BicarbonateHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 18464913methyl 2-methoxy-5-(4H-triazol-4-yl)benzoate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

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-4-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-ce714bb4058747aba38f044ce9a79828
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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