HCID 86751457, compound → Cryptolepine

HRID 1490266Notes

Reaction equation

HRID 1490266 reaction equation
I.[CH3:2][NH+:3]1[C:19]2[C:11]([N:12]=[C:13]3[C:18]=2[CH:17]=[CH:16][CH:15]=[CH:14]3)=[CH:10][C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2>C([O-])([O-])=O.[Na+].[Na+]>[CH3:2][N:3]1[C:19]2[C:11]([N:12]=[C:13]3[C:18]=2[CH:17]=[CH:16][CH:15]=[CH:14]3)=[CH:10][C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2

Participants

3

Reactant 1

HCID 86751457HCID 86751457, compound

Product 1

HCID 82143CryptolepineYield 51.3%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

5-Methylquindolinium hydroiodide (1.5 g, 4.2 mmol) from Example 3 was shaken with a 5% solution of Na2CO3 (100 mL) and extracted with chloroform (2×200 mL). The extract of the free base was purified on a basic alumina column using chloroform to elute the quindoline impurity; elution with 1-2% methanol in chloroform gave 0.5 g of the title compound as a purple solid, mp 178°-180° C. [lit 166°-169° C. (Gellert, E.; Raymond-Hamet; Schlittler, E. Helv. Chim. Acta 1951, 34, 642-651)]; 1H NMR (DMSO-d6) δ 8.92 (s, H11), 8.50 (d, J=9.2, 1H, H4), 8.47 (d, J=8.4, 1H, H6), 8.38 (d, J=8.4, 1H, H1), 7,89 (t, J=7.6, 1H, H3), 7.69-7.64 (m, 2H, H2 and H9), 7.52 (t, J=8.4, 1H, H8), 7.02 (t, J=8.4, 1H, H7), 4.90 (s, 3H, NCH3); 13C NMR (DMSO-d6) δ 160.46, 144.76, 138.96, 132.56, 130.13, 129.47, 128.66, 126.15, 124.97, 124.26, 123.60, 119.30, 116.36, 116.23, 113.64, 38.73.

Workup

  1. extractionextracted with chloroform (2×200 mL)
  2. extractionThe extract of the free base
  3. customwas purified on a basic alumina column
  4. washto elute the quindoline impurity
  5. washelution with 1-2% methanol in chloroform

Sources & evidence

ORD record
ord-31b5625dfaa5403ca91ebbea054279f7
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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