Sodium Iodide → HCID 86753922, compound

HRID 1418696Notes

Reaction equation

HRID 1418696 reaction equation
Cl[CH2:2][C:3]([O:5][CH:6]([C:9]1[CH:25]=[C:24]2[N:12]([CH2:13][C:14]3[C:15]2=[N:16][C:17]2[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11](=[O:26])[C:10]=1[CH3:27])[CH2:7][CH3:8])=[O:4].[I-:28].[Na+]>CC(C)=O>[I:28][CH2:2][C:3]([O:5][CH:6]([C:9]1[CH:25]=[C:24]2[N:12]([CH2:13][C:14]3[C:15]2=[N:16][C:17]2[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11](=[O:26])[C:10]=1[CH3:27])[CH2:7][CH3:8])=[O:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 86753923HCID 86753923, compound

Product 1

HCID 86753922HCID 86753922, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of (±)-7-[1-[(chloroacetyl)oxy]propyl]-8-methylindolizino[1,2-b]quinolin-9(11H)-one (100 mg, 0.26 mmol) in acetone (10 mL) was added sodium iodide (150 mg, 1.0 mmol), and the resulting solution was heated at reflux for 1 h. Upon cooling, a solid precipitate appeared. The solvent was removed in vacuo, and the residue was partitioned between CH2Cl2 and H2O. The organic extract was washed with H2O (3×), dried over sodium sulfate and concentrated under reduced pressure to afford the title compound. 1H NMR (CDCl3) d 8.35 (s, 1H), 8.22 (d, J=8.2 Hz, 1H), 7.92 (d, J=8.0 Hz, 1H), 7.81 (m, 1H), 7.66 (m, 1H), 7.38 (s, 1H), 5.91 (dd, J=7.9, 6.0 Hz, 1H), 5.26 (two s, 2H), 3.84 (d, J=10.1 Hz, 1H), 3.75 (d, J=10.1 Hz, 1H), 2.36 (s, 3H), 2.10-1.83 (m, 2H), 1.03 (t, J=7.4 Hz, 3H). Anal. Calcd for C21H19IN2O3.1/2 H2O: C, 52.19; H, 4.17; N, 5.80. Found: C, 52.16; H, 4.05; N, 5.39.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for 1 h
  3. temperatureUpon cooling
  4. customThe solvent was removed in vacuo
  5. customthe residue was partitioned between CH2Cl2 and H2O
  6. extractionThe organic extract
  7. washwas washed with H2O (3×)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2af678dd12d54a2c993c062522e788d2
Source dataset
uspto-grants-1999_03
Patent number
US05883255

Reaction notes

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