Hydrazine hydrate (1:1) → 4'-Methylbiphenyl-2-carbohydrazide

HRID 1870917Notes

Reaction equation

HRID 1870917 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([OH:16])=O)=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.O.[NH2:24][NH2:25]>O1CCCC1.CN(C)C=O.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:24][NH2:25])=[O:16])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 65578Oxalyl chlorideHCID 815682-(4-Methylphenyl)benzoic acid

Product 1

HCID 13937904'-Methylbiphenyl-2-carbohydrazideYield 63%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4'-methylbiphenyl-2-carboxylic acid (6.4 g) in tetrahydrofuran (50 ml) were added N,N-dimethylformamide (two drops) and oxalyl chloride (4.4 g). The mixture was stirred for 16 hours at room temperature. The solvent was evaporated to dryness under reduced pressure to give an oil, which was added dropwise to a solution of hydrazine monohydrate (7.5 g) in tetrahydrofuran (50 ml) with stirring, followed by stirring for further 6 hours. The reaction mixture was diluted with water, which was extracted with ethyl acetate. The extract was washed with water and dried. The solvent was evaporated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel to give crude crystals. Recrystallization from chloroform-isopropyl ether afforded the title compound as colorless needles (4.3 g, 63%), m.p.98-99° C.

Workup

  1. customThe solvent was evaporated to dryness under reduced pressure
  2. customto give an oil, which
  3. stirringwith stirring
  4. stirringby stirring for further 6 hours
  5. extractionwas extracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. customThe solvent was evaporated to dryness under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel
  10. customto give crude crystals
  11. customRecrystallization from chloroform-isopropyl ether

Sources & evidence

ORD record
ord-b85735b0c4bd4e7588a9e188d80136c5
Source dataset
uspto-grants-2000_08
Patent number
US06100252

Reaction notes

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