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HRID 260198Notes

Reaction equation

HRID 260198 reaction equation
[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.C([O-])(=O)[C:22]1[CH:27]=[CH:26][CH:25]=[N:24][CH:23]=1.[CH3:30][I:31].C[C:33](C)=[O:34]>>[I-:31].[CH3:30][N:24]1[CH:23]=[CH:22][CH:27]=[CH2+:26][CH:25]1[C:33]([O:20][C:9]1[CH:8]=[CH:7][C:6]2[C@@H:5]3[C@H:14]([C@H:15]4[C@@:2]([CH2:3][CH2:4]3)([CH3:1])[C:18](=[O:19])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)=[O:34]

Participants

3

Reactant 3

HCID 180AcetoneHCID 6328Methyl iodideHCID 86740294HCID 86740294, compound

Product 0

No Product data yet.

Procedure

To estrone nicotinate (0.5 g, 0.0013 mol) in acetone (20 ml) was added methyl iodide (1 ml, 0.016 mol) and the mixture was refluxed overnight. The deep yellow precipitate was filtered, washed with acetone, and dried. Yield 90% (0.6226 g); m.p. 245°-248° C. (dec.). NMR (d5 -DMSO) δ 9.8-9.7 (br s, 1H, C2 pyridinium proton), 9.4-9.0 (m, 2H, C4, C6 pyridinium protons), 8.4-8.0 (m, 1H, C5 pyridinium proton), 7.4-7.2 (m, 1H, C1 estrone proton), 7.1-6.9 (m, 2H, C2,4 estrone protons), 3.2-1.3 (estrone skeletal protons, 15), 1.0-0.9 (s, 3H, C18 estrone protons). IR (KBr) 1755-1740 (broad C=O stretching). Anal. calculated for C25H28NO3I: C, 58.03; H, 5.47; N, 2.71. Found: C, 58.16; H, 5.51; N, 2.67. The product has the formula: ##STR1466##

Workup

  1. temperaturethe mixture was refluxed overnight
  2. filtrationThe deep yellow precipitate was filtered
  3. washwashed with acetone
  4. customdried

Sources & evidence

ORD record
ord-12c6fe906e2e4f26ba16d9e367215286
Source dataset
uspto-grants-1996_06
Patent number
US05525727

Reaction notes

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