Fumaric Acid → HCID 67022769, compound

HRID 406954Notes

Reaction equation

HRID 406954 reaction equation
[CH2:1]([O:3][C:4]1[CH:17]=[C:16]2[C:7]([C:8]([C:19]3[CH:20]=[CH:21][C:22](=[O:26])[N:23]([CH3:25])[CH:24]=3)=[N:9][C@H:10]3[C@@H:15]2[CH2:14][C@H:13]([OH:18])[CH2:12][CH2:11]3)=[CH:6][C:5]=1[O:27][CH3:28])[CH3:2].[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33]>CC(C)=O.C(O)(C)C>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33].[CH2:1]([O:3][C:4]1[CH:17]=[C:16]2[C:7]([C:8]([C:19]3[CH:20]=[CH:21][C:22](=[O:26])[N:23]([CH3:25])[CH:24]=3)=[N:9][C@H:10]3[C@@H:15]2[CH2:14][C@H:13]([OH:18])[CH2:12][CH2:11]3)=[CH:6][C:5]=1[O:27][CH3:28])[CH3:2]

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 11853253HCID 11853253, compound

Product 1

HCID 67022769HCID 67022769, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 3776IsopropanolSolvent

Procedure

5-((2R,4aR,10bR)-9-Ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydro-phenanthridin-6-yl)-1-methyl-1H-pyridin-2-one (38.2 mg, 0.1 mmol) are dissolved in 0.5 ml of acetone. 12.8 mg (0.11 mmol) of fumaric acid (dissolved in 0.5 ml of a 82:18 mixture of acetone and isopropanol) are added. The crystals are filtered off and dried to obtain 25.6 mg (51%) of the title compound (m.p.: 156° C.).

Workup

  1. additionare added
  2. filtrationThe crystals are filtered off
  3. customdried

Sources & evidence

ORD record
ord-4644532de25a45009cf184dae4852b66
Source dataset
uspto-grants-2014_06
Patent number
US08754218B2

Reaction notes

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