Hydrogen Bromide → HCID 178419732, compound

HRID 1009080Notes

Reaction equation

HRID 1009080 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]C)[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]([OH:20])=[CH:6][CH:7]=1

Participants

5

Reactant 3

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

Product 1

HCID 178419732HCID 178419732, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

1,3-Dioxo-2-(2,6-dihydroxypyridin-3-yl)-isoindoline hydrobromide (7) was prepared and isolated as follows. To a flask were added 2,6-dimethoxy-3-phthalimidopyridine (150 mg, 0.528 mmol) and hydrogen bromide solution in acetic acid (30%, 6 ml). The mixture was stirred at an 70° C. oil bath under N2 for 54 h. The mixture was cooled to room temperature, dry ether was added, and the supernatant liquid was decanted. Then ethyl acetate was added, solid precipitated, filtered and washed with ethyl acetate to afford 7 (126 mg, 71%) as a white solid: 1H NMR (CD3OD) δ 7.83-7.77 (m, 4H), 6.37 (d, J=8.1 Hz, 1H), 6.37 (d, J=8.1 Hz, 1H); MS (CI/CH4) 256 [M]+; HRMS (DEI) m/z calcd for C13H8N2O4 256.0484. found 256.0483.

Workup

  1. custom1,3-Dioxo-2-(2,6-dihydroxypyridin-3-yl)-isoindoline hydrobromide (7) was prepared
  2. customisolated
  3. temperatureThe mixture was cooled to room temperature
  4. customthe supernatant liquid was decanted
  5. additionThen ethyl acetate was added
  6. customsolid precipitated
  7. filtrationfiltered
  8. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-73131010a2164e048bb1603f884552d4
Source dataset
uspto-grants-2011_07
Patent number
US07973057B2

Reaction notes

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