Ethanol → HCID 67596585, compound

HRID 582656Notes

Reaction equation

HRID 582656 reaction equation
[I-].CO[C:4]1[C:20]2[C:8](=[CH:9][C:10]3[N:11](C(=O)C)[C:12]4[C:17]([C:18]=3[NH+:19]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:7]=[CH:6][CH:5]=1.[C:24]([O-:27])([O-])=O.[Na+].[Na+].[CH2:30](O)C>>[CH3:24][O:27][C:16]1[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=1)=[N:11][C:10]1[C:18]=2[N:19]([CH3:30])[C:20]2[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=2[CH:9]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 10340Sodium CarbonateHCID 67598258HCID 67598258, compound

Product 1

HCID 67596585HCID 67596585, compound

Procedure

A solution of 4-methoxy-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 (MH+).

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-1c6d4313698c4a1292469bf23a1dd29b
Source dataset
uspto-grants-1999_07
Patent number
US05925647

Reaction notes

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