Hydrochloric Acid → 1-(5-chloro-2-methylphenyl)-3-methyl-1H-pyrazol-5-amine

HRID 1466561ノート

反応式

HRID 1466561 の反応式
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:11])=[C:7]([NH:9][NH2:10])[CH:8]=1.Cl.[CH3:13]/[C:14](/N)=[CH:15]\[C:16]#[N:17].C(=O)(O)[O-].[Na+]>C(O)C>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:11])=[C:7]([N:9]2[C:16]([NH2:17])=[CH:15][C:14]([CH3:13])=[N:10]2)[CH:8]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 53247203-AminocrotonitrileHCID 13200574(5-Chloro-2-methylphenyl)hydrazine hydrochloride

生成物 1

HCID 580631601-(5-chloro-2-methylphenyl)-3-methyl-1H-pyrazol-5-amine

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

To a solution of (5-chloro-2-methylphenyl)hydrazine hydrochloride (1.49 g, 7.72 mmol, 1 eq) in 8 mL ethanol was added hydrogen chloride (4.0 mL of a 5 M aqueous solution, 20 mmol, 2 eq) and 3-aminocrotonitrile (0.664 g, 8.09 mmol, 1.05 eq). The reaction mixture was stirred at 80° C. for 16 hours and then brought to neutral pH with saturated aqueous sodium bicarbonate. The resulting solution was extracted twice with dichloromethane, and the combined extracts were dried over magnesium sulfate and concentrated to give 1-(5-chloro-2-methylphenyl)-3-methyl-1H-pyrazol-5-amine, which was carried forward without further purification. LCMS (ESI) m+H=222.2; 1H NMR (400 MHz, DMSO-d6) δ: 7.39 (d, 1H), 7.37 (d, 1H), 7.25 (s, 1H), 5.22 (s, 1H), 5.00 (s, 2H), 2.04 (overlapping s and s, 6H).

後処理

  1. extractionThe resulting solution was extracted twice with dichloromethane
  2. dry with materialthe combined extracts were dried over magnesium sulfate
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-dfaddd3afef643b8b0a754fd6ff78d90
出典データセット
uspto-grants-2015_04
特許番号
US08999998B2

反応ノート

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