Ammonia → 3-(4-Methoxybenzyl)-1-isoquinolinone

HRID 432668Notes

Reaction equation

HRID 432668 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][C:8]2[O:9][C:10]([C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=O)=[CH:5][CH:4]=1.[NH3:21]>>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][C:8]2[NH:21][C:10](=[O:9])[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 187602473-(4-Methoxybenzyl)isocoumarin

Product 1

HCID 98784643-(4-Methoxybenzyl)-1-isoquinolinoneYield 12%

Conditions

Temperature
150 °C

Procedure

A stirred suspension of 3-(4-methoxybenzyl)isocoumarin (0.35 g, 1.3 mmol) in 15% methanolic ammonia solution (100 ml) was heated at 150° C. in a 300 ml autoclave for 5 hours then cooled to ambient temperature. The resulting solid was collected by filtration, washed with a little cold methanol and dried in vacuo to give 3-(4-methoxybenzyl)-1-isoquinolinone (0.04 g, 12%) as a solid; m.pt. 216-218° C.; δH 3.80 (3H, s), 3.85 (2H, s), 6.25 (1H, s), 6.90 (2H, d, J=8.2 Hz), 7.30 (2H, d), 7.30-7.60 (3H, m), 8.20 (1H, d), 11.20 (1H, br s); m/z (M+H)+. 266 (100% purity).

Workup

  1. temperaturethen cooled to ambient temperature
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with a little cold methanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-8dabe2c67cad44bab2105c1114311e5f
Source dataset
uspto-grants-2003_12
Patent number
US06664269B2

Reaction notes

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