2-Acetoxybenzoyl chloride → HCID 178470450, compound

HRID 442343Notes

Reaction equation

HRID 442343 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[N:7][C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:5]2[OH:17].[C:18]([O:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25])(=[O:20])[CH3:19]>N1C=CC=CC=1>[C:18]([O:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[N:7][C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:5]2[OH:17])=[O:25])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 796682-Acetoxybenzoyl chlorideHCID 178470447HCID 178470447, compound

Product 1

HCID 178470450HCID 178470450, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of ethyl 6-amino-4-hydroxycinnolin-3-yl carboxylate (1.0 g.) in dry pyridine (20 ml.) was added o-acetoxybenzoylchloride (0.8 g), and the mixture was stirred at room temperature for 16 hours. The solution was then heated to 100° C. for 1 hr., cooled to 20° C. and poured into a mixture of ice and excess N-HCl. The mixture was filtered and the solid residue crystallised from aqueous ethanol to give ethyl 6-o-acetoxybenzamido-4-hydroxycinnolin-3-yl carboxylate, m.p. 240°-2° C.

Workup

  1. temperatureThe solution was then heated to 100° C. for 1 hr
  2. temperature, cooled to 20° C.
  3. filtrationThe mixture was filtered
  4. customthe solid residue crystallised from aqueous ethanol

Sources & evidence

ORD record
ord-d5be695c26c541c0a97d3bcd9169a1c9
Source dataset
uspto-grants-1977_08
Patent number
US04045439

Reaction notes

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