HCID 86751461, compound → HCID 10681089, compound

HRID 1490270Notes

Reaction equation

HRID 1490270 reaction equation
Cl.[CH3:2][N:3]1[C:19]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[CH:16]3)=[NH+:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2>C([O-])([O-])=O.[Na+].[Na+]>[CH3:2][N:3]1[C:19]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[CH:16]3)=[N:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

3

Reactant 1

HCID 86751461HCID 86751461, compound

Product 1

HCID 10681089HCID 10681089, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

The 10-methylquindolinium hydrochloride obtained above (250 mg, 0.9 mmol) was shaken with an aqueous 5% Na2CO3 solution (50 mL), extracted with ethyl ether (2×50 mL) and purified by HPLC (ethyl acetate-hexane 1:6) to give 100 mg (45.5%) of 10-methylquindoline; 1 H NMR (CDCl3) δ 8.56 (d, J=7.6, H, H8), 8.34 (d, J=8.4, 1H, H4), 7.94 (d, J=8.0, 1H, H1), 7.85 (s, 1H, H11), 7.69-7.61 (m, 2H, H3 and H6), 7.56 (t, J=7.2, 1H, H2), 7.37 (d, J=8.4, 1H, H9), 7.33 (t, J=7.6, 1H, H7), 3.82 (s, 3H, CH3); 13C NMR (CDCl3) δ 145.89, 144.84, 143.92, 133.98, 129.60, 129.12, 127.08, 126.75, 126.12, 125.14, 121.96, 121.47, 119.58, 110.58, 108.34, 28.98; MS (EI, m/z) 232.1 (M+).

Workup

  1. extractionextracted with ethyl ether (2×50 mL)
  2. custompurified by HPLC (ethyl acetate-hexane 1:6)

Sources & evidence

ORD record
ord-174fe5d8b6814230a9243d629f9b3896
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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