p-Toluidine → 6-METHYLQUINOLIN-2(1H)-ONE

HRID 1432848Notes

Reaction equation

HRID 1432848 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[C:9](Cl)(=[O:18])[CH:10]=[CH:11]C1C=CC=CC=1>>[CH3:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][C:9](=[O:18])[CH:10]=[CH:11]2

Participants

3

Reactant 2

HCID 7813p-ToluidineHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 122374586-METHYLQUINOLIN-2(1H)-ONE

Procedure

The title compound is prepared from p-toluidine and cinnamoyl chloride according to the procedure described in Synthesis 1975, 739. The crude product obtained is triturated in Et2O/hexanes and filtered to give the title compound as a beige solid. 1H NMR (DMSO-d6, 300 MHz) δ11.60 (bs, 1H), 7.82 (d, 1H), 7.41 (s, 1H), 7.30 (d, 1H), 7.18 (d, 1H), 6.45 (d, 1H), 2.30 (s, 3H).

Workup

  1. customdescribed in Synthesis 1975, 739
  2. customThe crude product obtained

Sources & evidence

ORD record
ord-185242744b1c4d6a9c4b4179f9c6e02c
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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