HCID 22066011, compound → HCID 22066009, compound

HRID 1828258Notes

Reaction equation

HRID 1828258 reaction equation
[CH:1]([O:4][C:5]1[CH:20]=[C:19]2[C:21]3[CH:15]([N:16]([CH3:22])[CH2:17][CH2:18]2)[C:14](=[O:23])[C:13]2[C:8](=[CH:9][C:10]([O:28][CH3:29])=[C:11]([O:24]C(C)C)[CH:12]=2)[C:7]=3[C:6]=1[O:30][CH3:31])([CH3:3])[CH3:2]>C(O)(=O)C.S(=O)(=O)(O)O>[OH:24][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][C:10]=1[O:28][CH3:29])[C:7]1=[C:21]3[CH:15]([N:16]([CH3:22])[CH2:17][CH2:18][C:19]3=[CH:20][C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[C:6]1[O:30][CH3:31])[C:14]2=[O:23]

Participants

3

Reactant 1

HCID 22066011HCID 22066011, compound

Product 1

HCID 22066009HCID 22066009, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 23350293Acetic acid sulfuric acidSolvent

Procedure

The solution of compound (3) (50 mg) in acetic acid-sulfuric acid solution (96:4, 5 ml) was refluxed for 1 hour under nitrogen. After cooling to room temperature, the solution was evaporated under vacuum. The residue was neutralized with ammonia water and extracted with chloroform (100 ml ×2). The combined chloroform layers were washed with water (50 ml×2), dried over anhydrous sodium sulfate, concentrated under reduced pressure. The residue obtained was purified on a silica gel column and eluted with chloroform-methanol (99:3) to obtain a brown solid, 9-hydroxy-2-isopropyloxy-1,10-dimethoxy-7-oxoaporphine (4) (10 mg, 22% yield): m.p. 240–242° C.; IR(KBr) νmax 3422, 3008, 2977, 2932, 1728, 1651, 1593, 1513, 1461, 1417, 1380, 1351, 1280, 1247, 1213, 1149, 1116, 1059, 1013, 932, 894, 866, 822 cm−1; 1H NMR (200 MHz, CD3OD) δ 1.51 (6H, d, J=6.0 Hz, 2×CH3), 4.01 (3H, s, OCH3), 4.02 (3H, s, OCH3), 4.87 (1H, m, OCH), 7.25 (1H, s, H-3), 7.74 (1H, s, H-8), 7.83 (1H, d, J=4.8 Hz, H-4), 8.63 (1H, d, J=4.8 Hz, H-5), 8.68 (1H, s, H-11); ESI MS (positive): [M+H]+ 366.

Workup

  1. customthe solution was evaporated under vacuum
  2. extractionextracted with chloroform (100 ml ×2)
  3. washThe combined chloroform layers were washed with water (50 ml×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified on a silica gel column
  8. washeluted with chloroform-methanol (99:3)

Sources & evidence

ORD record
ord-f3ae6ccb50a84043929e9fdac2450113
Source dataset
uspto-grants-2006_06
Patent number
US07057044B2

Reaction notes

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