Sodium Azide → 4-Hydroxy-7-methoxy-3-(4-methoxyphenyl)isoquinolin-1(2H)-one

HRID 333673Notes

Reaction equation

HRID 333673 reaction equation
N([O-])=[O:2].[Na+].N[C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C:9](=[O:18])[NH:8][C:7]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1.[N-]=[N+]=[N-].[Na+]>O.C(O)(=O)C.S(=O)(=O)(O)O>[OH:2][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C:9](=[O:18])[NH:8][C:7]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1

Participants

7

Reactant 3

HCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 533806664-amino-7-methoxy-3-(4-methoxyphenyl)isoquinolin-1(2H)-one

Product 1

HCID 533793614-Hydroxy-7-methoxy-3-(4-methoxyphenyl)isoquinolin-1(2H)-one

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×HCID 1118Sulfuric AcidSolvent

Procedure

At 0° C., a solution of sodium nitrite (24.8 mg, 0.36 mmol) in water (0.5 mL) is added slowly to a solution of 4-amino-7-methoxy-3-(4-methoxyphenyl)isoquinolin-1(2H)-one (100 mg, 0.33 mmol) dissolved in acetic acid (1 mL) and sulphuric acid (0.5 mL). The mixture is left under stirring under cold conditions for 30 minutes then sodium azide (25.7 mg, 0.39 mmol) dissolved in a minimum amount of water (0.2 mL) is introduced slowly. Stirring, still under cold conditions, is maintained for another 3 hours, then water (10 mL) is poured onto the reaction mixture and the solid residue formed is collected by filtration. Silica gel column chromatography using a gradient of ethanol (0 to 2%) in CH2Cl2 as eluent makes it possible to isolate the compound possessing the greatest mobility which corresponds to the expected compound 41 (31 mg, 31%) in the form of a white solid, 1H NMR (CDCl3) 7.91 (1H, d), 7.74 (1H, d), 7.41 (2H, d), 7.16 (1H, dd), 6.85 (2H, d), 6.75 (1H, br s), 4.60 (1H, br s), 3.98 (3H, s), 3.78 (3H, s); MS 295 (M−2H).

Workup

  1. waitThe mixture is left
  2. additionis introduced slowly
  3. stirringStirring, still under cold conditions
  4. temperatureis maintained for another 3 hours
  5. customthe solid residue formed
  6. filtrationis collected by filtration
  7. customto isolate the compound

Sources & evidence

ORD record
ord-66858ffec2d144a19238e9b96bae130d
Source dataset
uspto-grants-2014_11
Patent number
US08883763B2

Reaction notes

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