Water → 5-Ethynyl-2-methylaniline

HRID 2367148ノート

反応式

HRID 2367148 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10]C(C)(O)C)[CH:5]=[CH:6][C:7]=1[CH3:8].[OH-].[K+].O>C1(C)C=CC=CC=1.CCOCC>[C:9]([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH:3]=1)[NH2:1])#[CH:10]

参加物

6

反応物 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 67044587HCID 67044587、化合物

生成物 1

HCID 189250605-Ethynyl-2-methylaniline

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

A solution of 4-(3-amino-4-methylphenyl)-2-methylbut-3-yn-2-ol (509 mg, 2.7 mmol) in toluene (2 mL) was treated with potassium hydroxide (1.0 g, 18 mmol) at reflux for 20 min. After cooling to rt, water and ether were added, and the layers were partitioned. The organic phase was acidified with 4 N hydrochloric acid in dioxane (700 μL). The volatile materials were removed in vacuo providing a yellow/brown solid. The solid was taken up in ether and washed with saturated sodium bicarbonate. The organic phase was dried over magnesium sulfate, filtered, and concentrated carefully to avoid loss of the moderately volatile product. Desired 5-ethynyl-2-methylaniline was isolated as an oil in quantitative yield, contaminated with 10% ether by mass. 1H NMR (400 MHz, CDCl3): 6.99 (d, 1H), 6.85 (dd, 1H), 6.81 (d, 1H), 3.61 (br s, 2H), 2.98 (s, 1H), 2.16 (s, 3H); GCMS for C9H9N: 131 (M+).

後処理

  1. temperatureat reflux for 20 min
  2. customthe layers were partitioned
  3. customThe volatile materials were removed in vacuo
  4. customproviding a yellow/brown solid
  5. washwashed with saturated sodium bicarbonate
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated carefully

出典と根拠

ORDレコード
ord-ec86594163034c028767aee2a5d0267b
出典データセット
uspto-grants-2014_04
特許番号
US08697737B2

反応ノート

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