Hydrazine → 2-Chloro-4-(5-methyl-1h-[1,2,4]triazol-3-yl)-benzoic acid methyl ester

HRID 1978203Notes

Reaction equation

HRID 1978203 reaction equation
[NH2:1]N.[CH3:3][O:4][C:5](=[O:21])[C:6]1[CH:19]=[CH:18][C:9]([C:10]([N:12]=[C:13]([N:15](C)C)[CH3:14])=O)=[CH:8][C:7]=1[Cl:20]>C(O)(=O)C>[CH3:3][O:4][C:5](=[O:21])[C:6]1[CH:19]=[CH:18][C:9]([C:10]2[N:12]=[C:13]([CH3:14])[NH:15][N:1]=2)=[CH:8][C:7]=1[Cl:20]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 542321062-Chloro N-(1-dimethylaminoethylidene)-terephthalamic acid methyl ester

Product 1

HCID 540153042-Chloro-4-(5-methyl-1h-[1,2,4]triazol-3-yl)-benzoic acid methyl esterYield 67.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

Anhydrous hydrazine (0.30 mL, 9.6 mmol) was added via syringe to a solution of the intermediate of Step B (4.8 mmol) in glacial acetic acid (6 mL) under a nitrogen atmosphere. The reaction was heated at 90° C. for 30 minutes, then cooled and concentrated in vacuo to a light brown solid. The solid was redissolved in aqueous methanol and the solution neutralized with saturated aqueous sodium bicarbonate. The mixture was extracted with dichloromethane and ethyl actate, the extracts were combined and dried over sodium sulfate. Evaporation of the solvents yielded a solid which was triturated with ether to provide the title product (0.81 g) as an off-white solid, m.p. 196-198° C.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo to a light brown solid
  3. dissolutionThe solid was redissolved in aqueous methanol
  4. extractionThe mixture was extracted with dichloromethane and ethyl actate
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solvents
  7. customyielded a solid which
  8. customwas triturated with ether

Sources & evidence

ORD record
ord-cd359d74f0f94fdea3c86d0e62175b0c
Source dataset
uspto-grants-2001_05
Patent number
US06235900B1

Reaction notes

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