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

HRID 1418603노트

반응식

HRID 1418603 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

HCID 13937904'-Methylbiphenyl-2-carbohydrazide수율 63%

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9e120b62a867407c97bc900e74a6bc62
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05883111

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