Diethyl Ether → HCID 178470454, compound

HRID 442344Notes

Reaction equation

HRID 442344 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=O)=[O:3].[NH2:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[N:16][C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:14]2[OH:26].CCOCC>N1C=CC=CC=1>[OH:26][C:14]1[C:13]2[C:18](=[CH:19][CH:20]=[C:11]([NH:10][S:2]([CH3:1])(=[O:5])=[O:3])[CH:12]=2)[N:17]=[N:16][C:15]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 81560Methanesulfonic anhydrideHCID 178470447HCID 178470447, compound

Product 1

HCID 178470454HCID 178470454, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonic anhydride (1.392 g.) was added to a solution of ethyl 6-amino-4-hydroxycinnolin-3-yl carboxylate (0.932 g.) in dry pyridine (20 ml.), and the mixture was stirred at room temperature overnight. The resulting solution was poured into ether (500 ml.) and the amorphous solid which precipitated was filtered off and applied to a silica column (100 g. Kieselgel 60). Elution with a mixture of 15% v/v ethanol and 85% v/v chloroform, and evaporation of the appropriate fractions gave ethyl 4-hydroxy-6-(methanesulphonylamino)cinnolin-3-yl carboxylate, m.p. 274°-5° C.

Workup

  1. customthe amorphous solid which precipitated
  2. filtrationwas filtered off
  3. washElution
  4. additionwith a mixture of 15% v/v ethanol and 85% v/v chloroform, and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-a7bd4d015b54435dba6e586874b59172
Source dataset
uspto-grants-1977_08
Patent number
US04045439

Reaction notes

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