Sodium Carbonate → HCID 67596585, compound

HRID 1490290Notes

Reaction equation

HRID 1490290 reaction equation
[I-].[CH3:2][O:3][C:4]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:5]=1[C:6]1[N+:7]([CH3:24])=[C:8]3[C:13](=[CH:14][C:15]=1[N:16]2C(=O)C)[CH:12]=[CH:11][CH:10]=[CH:9]3.C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[CH3:2][O:3][C:4]1[C:5]2[C:17]([CH:18]=[CH:19][CH:20]=1)=[N:16][C:15]1[C:6]=2[N:7]([CH3:24])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[CH:14]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 21481068HCID 21481068, compound

Product 1

HCID 67596585HCID 67596585, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-methoxy-5-methyl-10-acetylquindolinium iodide obtained in Example 37 dissolved in approximately 50 mL of ethanol-free chloroform was adsorbed onto anhydrous Na2CO3 (1 g/100 mg iodide salt) and applied to a column filled with basic alumina. The mixture was eluted with CHCl3 until the UV active impurities eluted. Elution with CHCl3 -MeOH (97:3) provided the title compound as a purple solid; 1H NMR (CDCl3) δ 8.74 (s, 1H), 8.22 (d, J=8.4, 1H), 7.85 (d, J=8.4, 1H), 7.73 (d, J=8.4, 1H), 7.57 (m, 1H), 7.48 (m, 1H), 7.18 (d, J=7.6, 1H), 7.08 (m, 1H), 5.07 (s, 3H) , 4.12 (s, 3H); 13C NMR (CDCl3) δ 159.8, 150.5 (2 carbons), 144.1, 141.5, 131.2, 127.2, 126.3, 124.4, 124.1, 122.2, 119.5, 117.6, 114.1, 109.4, 56.5, 45.3; MS (LSIMS, m/z) 263 (M+).

Workup

  1. additionfilled with basic alumina
  2. washThe mixture was eluted with CHCl3 until the UV active impurities
  3. washeluted
  4. washElution with CHCl3 -MeOH (97:3)

Sources & evidence

ORD record
ord-c77420d19f024b6f8d400d8ef493bae8
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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