Thiophene → Ethyl 4-hydroxy-6-thienylcinnolin-3-yl carboxylate

HRID 442342Notes

Reaction equation

HRID 442342 reaction equation
[N+]([O-])(OCCCCC)=O.N[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].[S:27]1[CH:31]=[CH:30][CH:29]=[CH:28]1>>[OH:26][C:14]1[C:13]2[C:18](=[CH:19][CH:20]=[C:11]([C:28]3[S:27][CH:31]=[CH:30][CH:29]=3)[CH:12]=2)[N:17]=[N:16][C:15]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

4

Reactant 3

HCID 8030ThiopheneHCID 61250Amyl NitrateHCID 178470447HCID 178470447, compound

Product 1

HCID 178470438Ethyl 4-hydroxy-6-thienylcinnolin-3-yl carboxylate

Procedure

Amyl nitrate (1 ml.) was added to a stirred suspension of ethyl 6-amino-4-hydroxycinnolin-3-yl carboxylate (1 g.) in thiophen (100 ml.). The suspension was stirred and heated under reflux for 2 hours. The suspension was filtered whilst hot and the filtrate was evaporated, giving a brown crystalline residue. The solid was applied to a silica column (100 g. of Kieselgel 60) and eluted with a 10% v/v mixture of dry ethanol and chloroform. The appropriate fractions were evaporated, and the residue was crystallised from 1:1 v/v aqueous ethanol to give ethyl 4-hydroxy-6-thienylcinnolin-3-yl carboxylate, m.p. 258°-260° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. filtrationThe suspension was filtered whilst hot and the filtrate
  4. customwas evaporated
  5. customgiving a brown crystalline residue
  6. washeluted with a 10% v/v mixture of dry ethanol and chloroform
  7. customThe appropriate fractions were evaporated
  8. customthe residue was crystallised from 1:1 v/v aqueous ethanol

Sources & evidence

ORD record
ord-71b6488d48fa4cc2a2a7dddff62a0f46
Source dataset
uspto-grants-1977_08
Patent number
US04045439

Reaction notes

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