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

HRID 2183545

反応式

HRID 2183545 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9b402513c4384f52b727e614cf322e46
出典データセット
uspto-grants-2005_05
特許番号
US06900217B2

関連ノート

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