Hydrogen Bromide → HCID 21110584, compound

HRID 1766660Notes

Reaction equation

HRID 1766660 reaction equation
C[O:2][C:3]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[C:26]([CH3:27])=[CH:25][C:24]([N+:28]([O-:30])=[O:29])=[C:23]3[C:19]=2[CH2:20][CH2:21][CH2:22]3)=[CH:13][C:4]=1[CH2:5][C:6]1[CH:7]=[CH:8][C:9](=[O:12])[NH:10][N:11]=1.Br.O>C(O)(=O)C>[OH:2][C:3]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[C:26]([CH3:27])=[CH:25][C:24]([N+:28]([O-:30])=[O:29])=[C:23]3[C:19]=2[CH2:20][CH2:21][CH2:22]3)=[CH:13][C:4]=1[CH2:5][C:6]1[CH:7]=[CH:8][C:9](=[O:12])[NH:10][N:11]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 21110585HCID 21110585, compound

Product 1

HCID 21110584HCID 21110584, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 6-[2-methoxy-5-(5-methyl-7-nitroindan-4-yloxy)benzyl]-2H-pyridazine-3-one (704 mg) in acetic acid (10 mL) was added hydrobromic acid (48%, 10 mL). The mixture was heated at reflux temperature under an argon atmosphere overnight. After adding water, the reaction mixture was extracted with dichloromethane. The organic layer was washed with water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was crystallized from a small amount of ethyl acetate to give the title compound (270 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature under an argon atmosphere overnight
  3. extractionthe reaction mixture was extracted with dichloromethane
  4. washThe organic layer was washed with water and brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was crystallized from a small amount of ethyl acetate

Sources & evidence

ORD record
ord-1807a29bd0164a02a89f0ed9f6d8f6db
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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