Diazald → methyl 9-oxo-9h-xanthene-1-carboxylate

HRID 1596153Notes

Reaction equation

HRID 1596153 reaction equation
[N+](=C)=[N-].[CH3:4]N(N=O)S(C1C=CC(C)=CC=1)(=O)=O.[OH-].[K+].[O:20]=[C:21]1[C:34]2[C:33]([C:35]([OH:37])=[O:36])=[CH:32][CH:31]=[CH:30][C:29]=2[O:28][C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2>CO>[CH3:4][O:36][C:35]([C:33]1[C:34]2[C:21](=[O:20])[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:28][C:29]=2[CH:30]=[CH:31][CH:32]=1)=[O:37]

Participants

6

Reactant 4

HCID 6628DiazaldHCID 9550Diazomethane3×HCID 14797Potassium HydroxideHCID 470399HCID 470399, compound

Product 1

HCID 470401methyl 9-oxo-9h-xanthene-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Esterification of acid can be achieved by several conventional methods by those skilled in the art. These procedures include utilizing diazomethane or methyl alcohol catalyzed by mineral acids. For example, ethereal diazomethane solution can be prepared from N-methyl-N-nitrosotoluene-p-sulphonamide and potassium hydroxide from a water bath. 9-Oxoxanthene-1-carboxylic acid (1.29 g, 5 mmol) in absolute methanol is added to this ethereal diazomethane solution at 0° C. until a pale yellow color formed. Removal of the solvent provides the desired ester solid in 100% yield. Thus the final products, Examples 5-9, can be prepared by condensation hydrazine with the ketonester 11 as described in General procedure C.

Workup

  1. customformed
  2. customRemoval of the solvent

Sources & evidence

ORD record
ord-c0608b799e7c40a8804482a68bf8c7bf
Source dataset
uspto-grants-2001_09
Patent number
US06291425B1

Reaction notes

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