Ethanol → HCID 178470453, compound

HRID 442334Notes

Reaction equation

HRID 442334 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[N:9]=[N:8][C:7]=1[C:19]([OH:21])=[O:20].[CH2:22](O)[CH3:23]>>[OH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[N:9]=[N:8][C:7]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 178524932HCID 178524932, compound

Product 1

HCID 178470453HCID 178470453, compound

Procedure

Ethanol (200 ml.) was stirred at -40° C. and thionyl chloride (15 ml.) was added dropwise during 5 minutes. After a further 10 minutes at -40° C., 4-hydroxy-6-nitrocinnolin-3-yl carboxylic acid (10 g.) was added. The mixture was stirred overnight and allowed to warm to room temperature. The suspension was heated under reflux on a steam bath for 1 hour, and then kept at 0° C. for several hours. The solid was filtered off, and washed successively with ethanol (2 × 30 ml.) and ether (100 ml.) to give ethyl 4-hydroxy-6-nitrocinnolin-3-yl carboxylate, m.p. 294°-296° C.

Workup

  1. temperatureThe suspension was heated
  2. temperatureunder reflux on a steam bath for 1 hour
  3. waitkept at 0° C. for several hours
  4. filtrationThe solid was filtered off
  5. washwashed successively with ethanol (2 × 30 ml.) and ether (100 ml.)

Sources & evidence

ORD record
ord-619e2d54dd9f467a91ba96f82d7c0fc6
Source dataset
uspto-grants-1977_08
Patent number
US04045439

Reaction notes

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