Water → 5-Ethynyl-2-methylaniline

HRID 2367148노트

반응식

HRID 2367148 반응식
[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]

참가 물질

6

반응물 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 67044587HCID 67044587, 화합물

생성물 1

HCID 189250605-Ethynyl-2-methylaniline

시약·촉매·용매 2

HCID 1140Toluene용매HCID 3283Diethyl Ether용매2회

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-ec86594163034c028767aee2a5d0267b
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697737B2

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