Water → 5-Ethynyl-2-methylaniline

HRID 2261994Notes

Reaction equation

HRID 2261994 reaction equation
[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]

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 67044587HCID 67044587, compound

Product 1

HCID 189250605-Ethynyl-2-methylaniline

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-86500d69cac54b7cad0d1441f8c05246
Source dataset
uspto-grants-2010_12
Patent number
US07846959B2

Reaction notes

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