Benzonitrile, 3-(aminomethyl)- → HCID 54724186, compound

HRID 1867085Notes

Reaction equation

HRID 1867085 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[OH:11][C:12]1[CH:17]=[C:16]([CH3:18])[O:15][C:14](=O)[CH:13]=1>O>[OH:11][C:12]1[CH:17]=[C:16]([CH3:18])[N:7]([CH2:6][C:5]2[CH:4]=[C:3]([CH:10]=[CH:9][CH:8]=2)[C:2]#[N:1])[C:14](=[O:15])[CH:13]=1

Participants

4

Reactant 2

HCID 457594Benzonitrile, 3-(aminomethyl)-HCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54724186HCID 54724186, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A nitrogen flushed pyrex reaction tube was charged with 3-(aminomethyl)benzonitrile (1 g, 7.9 mmol), 4-hydroxy-6-methyl-2-pyrone (1 g, 7.9 mmol) and water (20 mL). The tube was capped and was heated to reflux. After 1.5 h, the product precipitated from solution. The reaction mixture was cooled to room temperature, filtered and washed with water. The product was used without further purification (1.67 g, 88%) 1H NMR (400 MHz, dmso-d6) δ 10.53 (s, 1H), 7.61 (d, J=8 Hz, 1H), 7.52 (t, J=8 Hz, 2H), 7.38 (d, J=8 Hz, 1H), 5.79 (dd, J=1 and 2.5 Hz, 1H), 5.56 (d, J=2.7 Hz, 1H), 5.18 (s, 2H), 2.14 (s, 3H) ppm. ES-HRMS m/z 241.0968 (M+H calcd for C14H13N2O2 requires 241.0972).

Workup

  1. customThe tube was capped
  2. temperaturewas heated to reflux
  3. customthe product precipitated from solution
  4. filtrationfiltered
  5. washwashed with water
  6. customThe product was used without further purification (1.67 g, 88%) 1H NMR (400 MHz, dmso-d6) δ 10.53 (s, 1H), 7.61 (d, J=8 Hz, 1H), 7.52 (t, J=8 Hz, 2H), 7.38 (d, J=8 Hz, 1H), 5.79 (dd, J=1 and 2.5 Hz, 1H), 5.56 (d, J=2.7 Hz, 1H), 5.18 (s, 2H), 2.14 (s, 3H) ppm

Sources & evidence

ORD record
ord-ea70b6febd944a5c94dcaf5d95a77139
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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