Citric Acid → HCID 23118686, compound

HRID 1178749Notes

Reaction equation

HRID 1178749 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][CH:5]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]1[C:19](=[O:21])[CH3:20].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1.O.[Li+].[OH-]>[C:19]([N:6]1[CH:5]([CH2:4][C:3]([OH:22])=[O:2])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]1=2)(=[O:21])[CH3:20]

Participants

6

Reactant 2

HCID 311Citric AcidHCID 68489381HCID 68489381, compound

Product 1

HCID 23118686HCID 23118686, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3939Lithium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (5-acetyl-5,6-dihydro-phenanthridin-6-yl)-acetic acid methyl ester (210 mg, 0.71 mmol) dissolved in a mixture of dioxane (10 mL) and water (10 mL), LiOH×H2O (42 mg, 1 mmol) was added. The solution was allowed to stir at r.t. for 4 h. Citric acid (5% solution in water) was added and the mixture was extracted with ethyl acetate. The organic phase was washed with citric acid (2×), water (1×), and brine (1×). After drying over MgSO4, the solvent was removed in vacuo to give a colourless oil that solidified on standing ar r.t. Yield, 70%. (+)-ESI-MS: m/z=282 [M+H]+, 240, 222, 180.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with citric acid (2×), water (1×), and brine (1×)
  4. dry with materialAfter drying over MgSO4
  5. customthe solvent was removed in vacuo
  6. customto give a colourless oil that
  7. customon standing ar r.t
  8. customYield

Sources & evidence

ORD record
ord-20b508c8cbbf497baca0cc3ded6eb46f
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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