Acetic Acid → HCID 135508885, compound

HRID 2305429Notes

Reaction equation

HRID 2305429 reaction equation
[C:1]1([N:7]2[C:16](=[O:17])[C:15]3[C:14]([OH:18])=[C:13]4[C:19]5[C:32]([CH2:33][CH2:34][C:12]4=[CH:11][C:10]=3[CH:9]=[N:8]2)=[C:31]([O:35][CH3:36])[C:30]2[C:29](=[O:37])[C:28]3[C:23](=[CH:24][C:25]([OH:40])=[C:26]([CH3:39])[C:27]=3[OH:38])[C:22](=[O:41])[C:21]=2[C:20]=5[OH:42])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl[C:46]([O:48][CH3:49])=[O:47].C(O)(=O)C>O>[C:1]1([N:7]2[C:16](=[O:17])[C:15]3[C:14]([OH:18])=[C:13]4[C:19]5[C:32]([CH2:33][CH2:34][C:12]4=[CH:11][C:10]=3[CH:9]=[N:8]2)=[C:31]([O:35][CH3:36])[C:30]2[C:29](=[O:37])[C:28]3[C:23](=[CH:24][C:25]([O:40][C:46]([O:48][CH3:49])=[O:47])=[C:26]([CH3:39])[C:27]=3[OH:38])[C:22](=[O:41])[C:21]=2[C:20]=5[OH:42])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 135487800HCID 135487800, compound

Product 1

HCID 135508885HCID 135508885, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 281.2 mg (0.5 mmol) of 2-phenyl-10,12,15,16-tetrahydroxy-8-methoxy-11-methyl-9,14-dioxo-6,7,9,14-tetrahydronaphthaceno[1,2-g]phthalazin-1-one (5) in 2 m of 2 M sodium hydroxide solution is diluted with 5 m of water. This solution is equilibrated at 5° C. and, while stirring, 2 m of methyl chloroformate are added. The mixture is subsequently stirred at room temperature for 30 min and then neutralized with acetic acid. The precipitated product is filtered off with suction to obtain 260 mg of the product. The yield is 84% of theory.

Workup

  1. customis equilibrated at 5° C.
  2. stirringThe mixture is subsequently stirred at room temperature for 30 min
  3. filtrationThe precipitated product is filtered off with suction

Sources & evidence

ORD record
ord-a4edf9af88c842a4933b27d41f2635aa
Source dataset
uspto-grants-2002_08
Patent number
US06440968B1

Reaction notes

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