Hydrochloric Acid → Ethyl 6-acetylamino-4-hydroxycinnolin-3-yl carboxylate

HRID 442337Notes

Reaction equation

HRID 442337 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[N:11][C:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:9]2[OH:21].Cl>N1C=CC=CC=1>[C:1]([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[N:11][C:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:9]2[OH:21])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 178470447HCID 178470447, compound

Product 1

HCID 178470449Ethyl 6-acetylamino-4-hydroxycinnolin-3-yl carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetyl chloride (0.6 ml.) was added to a stirred solution of ethyl 6-amino-4-hydroxycinnolin-3-yl carboxylate (0.932 g.) in dry pyridine (20 ml.). The solution was stirred at room temperature for 16 hours and then was poured onto a mixture of ice (100 g.) and 5N-hydrochloric acid (50 ml.). The mixture was kept at 4° C. for 4 hours, and the solid precipitate was then filtered off, washed with water (10 ml.), dried as much as possible on the filter, and recrystallised from ethanol to give ethyl 6-acetylamino-4-hydroxycinnolin-3-yl carboxylate, m.p. 280°-281° C.

Workup

  1. waitThe mixture was kept at 4° C. for 4 hours
  2. filtrationthe solid precipitate was then filtered off
  3. washwashed with water (10 ml.)
  4. customdried as much as possible on the filter
  5. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-c7829cf75f784f77891c1fbd078c24e0
Source dataset
uspto-grants-1977_08
Patent number
US04045439

Reaction notes

Loading…