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

HRID 442336Notes

Reaction equation

HRID 442336 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[N:18][C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:16]2[OH:28].Cl>N1C=CC=CC=1>[CH2:5]([O:4][C:2]([NH:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[N:18][C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:16]2[OH:28])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 178470447HCID 178470447, compound

Product 1

HCID 178470452Ethyl 6-benzyloxycarbonylamino-4-hydroxycinnolin-3-yl carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

Benzyl chloroformate (7.5 g.) was added to a stirred solution of ethyl 6-amino-4-hydroxycinnolin-3-yl carboxylate (4.66 g.) in pyridine (75 ml.). The solution was stirred for 18 hours at room temperature and for 2 hours at 100° C. The solution was cooled and was poured onto a mixture of ice (500 g.) and 5N-hydrochloric acid (200 ml.). The pale solid which was precipitated was filtered off, washed with water, and recrystallised from a mixture of ethanol and water to give ethyl 6-benzyloxycarbonylamino-4-hydroxycinnolin-3-yl carboxylate, m.p. 250°-252° C.

Workup

  1. temperatureThe solution was cooled
  2. customThe pale solid which was precipitated
  3. filtrationwas filtered off
  4. washwashed with water
  5. customrecrystallised from a mixture of ethanol and water

Sources & evidence

ORD record
ord-fde9f7cc143546298b8aeb8cde34c6ec
Source dataset
uspto-grants-1977_08
Patent number
US04045439

Reaction notes

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