Hydrochloric Acid → 2-(4-Chloro-2-oxo-1,2-dihydropyridin-3-yl)-6-methylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione

HRID 920504Notes

Reaction equation

HRID 920504 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8]C)[C:3]=1[C:10]1[NH:24][C:13]2=[CH:14][C:15]3[C:16](=[O:23])[N:17]([CH3:22])[C:18](=[O:21])[C:19]=3[CH:20]=[C:12]2[N:11]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[C:10]1[NH:11][C:12]2=[CH:20][C:19]3[C:18](=[O:21])[N:17]([CH3:22])[C:16](=[O:23])[C:15]=3[CH:14]=[C:13]2[N:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 666873032-(4-Chloro-2-methoxypyridin-3-yl)-6-methylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione

Product 1

HCID 1363406582-(4-Chloro-2-oxo-1,2-dihydropyridin-3-yl)-6-methylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-(4-Chloro-2-methoxypyridin-3-yl)-6-methylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione (2.0 g, 5.84 mmol) was suspended in 50 mL of 1,4-dioxane at rt. Concentrated HCl (10 mL) was added. The reaction mixture was stirred and heated to reflux for 6 h. Then, it was evaporated to dryness to afford a pale-yellow solid product as a HCl salt. MS: 327.9 [M−H]−. 1H NMR (DMSO-d6, 500 MHz): δ 8.11 (s, 2H), 8.01 (s, 1H), 7.77 (d, 1H, J=7.0 Hz), 6.63 (d, 1H, J=7.0 Hz), 3.06 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 h
  3. customThen, it was evaporated to dryness

Sources & evidence

ORD record
ord-d9bc5551d5264670b866d402393b1b4b
Source dataset
uspto-grants-2016_03
Patent number
US09273055B2

Reaction notes

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