Acetic Acid → 4-(2,4,6-Trimethyl-phenyl)-2H-pyrazol-3-ylamine

HRID 2183545노트

반응식

HRID 2183545 반응식
O=[CH:2][CH:3]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[CH3:14])[C:4]#[N:5].O.[NH2:16][NH2:17].C(O)(=O)C.Cl>C1C=CC=CC=1.O>[CH3:14][C:7]1[CH:8]=[C:9]([CH3:13])[CH:10]=[C:11]([CH3:12])[C:6]=1[C:3]1[CH:2]=[N:17][NH:16][C:4]=1[NH2:5]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 224743973-Oxo-2-(2,4,6-trimethyl-phenyl)-propionitrile

생성물 1

HCID 224743864-(2,4,6-Trimethyl-phenyl)-2H-pyrazol-3-ylamine수율 10.3%

시약·촉매·용매 2

HCID 241Benzene용매HCID 962Water용매

실험 절차

A mixture of 3-oxo-2-(2,4,6-trimethyl-phenyl)-propionitrile (2.300 g, 12.3 mmol), hydrazine hydrate (0.93 g) and glacial acetic acid (1.55 ml) in 20 ml benzene was heated at reflux for 4.5 hours. Reaction mixture was cooled to room temperature and 50 ml of 18.5% HCl in water was added. The benzene layer was separated and reextracted with 18.5% HCl. The aqueous layer were combined and neutralized with ammonium hydroxide and stirred at rt. overnight. Precipitate formed and was filtered to yield the title compound (0.256 g) as a yellow solid. The benzene layer was concentrated and purified through silica gel column using 5% methanol in chloroform as eluent to give an additional 1.450 g of the title compound; 1H NMR (CDCl3) ä 7.24(s, 1H), 6.95(s, 2H), 4.75(brs, 2H), 2.32(s, 3H), 2.13(s, 6H) ppm.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 4.5 hours
  3. customReaction mixture
  4. customThe benzene layer was separated
  5. customovernight
  6. customPrecipitate formed
  7. filtrationwas filtered

출처 및 근거

ORD 기록
ord-9b402513c4384f52b727e614cf322e46
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900217B2

반응 노트

불러오는 중…