Hydrogen Bromide → 1,3-Dioxo-2-(2-hydroxy-6-methoxypyridin-3-yl)-isoindoline hydrobromide

HRID 1009079Notes

Reaction equation

HRID 1009079 reaction equation
C[O:2][C:3]1[C:8]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])=[CH:7][CH:6]=[C:5]([O:20][CH3:21])[N:4]=1.[BrH:22].CCOCC>C(O)(=O)C>[BrH:22].[O:19]=[C:10]1[C:11]2[C:12](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:14])[N:9]1[C:8]1[C:3]([OH:2])=[N:4][C:5]([O:20][CH3:21])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 584566382,6-Dimethoxy-3-phthalimidopyridine

Product 1

HCID 1784195961,3-Dioxo-2-(2-hydroxy-6-methoxypyridin-3-yl)-isoindoline hydrobromideYield 67%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1,3-Dioxo-2-(2-hydroxy-6-methoxypyridin-3-yl)-isoindoline hydrobromide (6) was prepared and isolated as follows. To a flask were added 2,6-dimethoxy-3-phthalimidopyridine (155 mg, 0.546 mmol) and hydrogen bromide solution in acetic acid (30%, 6 ml). The mixture was stirred at room temperature under N2 for 18 h. Dry ether was added slowly until the solution became cloudy. White crystals were precipitated, filtered and washed with ether and ethyl acetate to afford 6 (127 mg, 67%) as white powdery crystals: mp 250° C.; 1H NMR (DMSO-d6) δ 7.97-7.94 (m, 2H), 7.91-7.88 (m, 2H), 7.64 (d, J=8.2 Hz, 1H), 6.25 (d, J=8.2 Hz, 1H), 3.86 (s, 3H); 13C NMR (DMSO-d6) δ 167.5, 162.1, 159.1, 142.8, 135.4, 132.1, 123.7, 108.2, 96.4, 54.8; MS (CI/CH4) 270 [M]+.

Workup

  1. custom1,3-Dioxo-2-(2-hydroxy-6-methoxypyridin-3-yl)-isoindoline hydrobromide (6) was prepared
  2. customisolated
  3. customWhite crystals were precipitated
  4. filtrationfiltered
  5. washwashed with ether and ethyl acetate

Sources & evidence

ORD record
ord-ff53d45d422d4b52ae2cbbc6153d069e
Source dataset
uspto-grants-2011_07
Patent number
US07973057B2

Reaction notes

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