Acetic Acid → HCID 67521085, compound

HRID 1925311Notes

Reaction equation

HRID 1925311 reaction equation
[I:1]I.[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[NH:11][CH:10]=[CH:9][C:8]2=[O:17].CC(O)=O>[OH-].[Na+]>[I:1][C:9]1[C:8](=[O:17])[C:7]2[C:12](=[CH:13][C:14]([O:15][CH3:16])=[C:5]([O:4][CH3:3])[CH:6]=2)[NH:11][CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 807IodineHCID 4596116,7-Dimethoxy-4-hydroxyquinoline

Product 1

HCID 67521085HCID 67521085, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of iodine (14.84 g, 58.48 mmol) in KI (20% aq, 100 mL) was added to a solution of 6,7-dimethoxyquinolin-4(1H)-one (10.00 g, 48.73 mmol) in 2 N NaOH (aq, 100 mL), and the solution stirred at RT for 17 h. The mixture was acidified with AcOH and the resulting dark purple mixture was filtered and washed with water. The dark purple filter cake was recrystallized from water to afford an off-white suspension. This material was filtered and dried to afford 3-iodo-6,7-dimethoxyquinolin-4(1H)-one as an off-white solid. MS (ESI, pos. ion) m/z: 332.1 (M+H). Mass Calc'd for C11H10INO3: 331.

Workup

  1. filtrationthe resulting dark purple mixture was filtered
  2. washwashed with water
  3. customThe dark purple filter cake was recrystallized from water
  4. customto afford an off-white suspension
  5. filtrationThis material was filtered
  6. customdried

Sources & evidence

ORD record
ord-1138cc36e0904d6985b59ac9beff0c2b
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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