Azobisisobutyronitrile → HCID 178468880, compound

HRID 463354Notes

Reaction equation

HRID 463354 reaction equation
[CH2:1]([C:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([OH:18])[C:10]2[C:5](=[C:6]([C:19]([F:22])([F:21])[F:20])[CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2].[Cl:23]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Cl:23][CH:1]([C:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([OH:18])[C:10]2[C:5](=[C:6]([C:19]([F:22])([F:20])[F:21])[CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 31398ChlorosuccinimideHCID 178468992HCID 178468992, compound

Product 1

HCID 178468880HCID 178468880, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 9.3 g of ethyl 2-ethyl-4-hydroxy-8-trifluoromethyl-3-quinoline-carboxylate, 200 ml of carbon tetrachloride, 4.2 g of N-chlorosuccinimide and 0.45 g of azobis-isobutyronitrile was stirred at 65° C. maximum for 5 hours under a lamp and was then cooled to 20° C. and was filtered. The filtrate was evaporated to dryness and the residue was taken up in methylene chloride. The mixture was washed with water, dried and evaporated to dryness. The residue was empasted with petroleum ether and dried to obtain 9 g of ethyl 2-(1-chloroethyl)-4-hydroxy-8-trifluoromethyl-3-quinoline-carboxylate melting at 104° C.

Workup

  1. temperaturewas then cooled to 20° C.
  2. filtrationwas filtered
  3. customThe filtrate was evaporated to dryness
  4. washThe mixture was washed with water
  5. customdried
  6. customevaporated to dryness
  7. customdried

Sources & evidence

ORD record
ord-6fb23fa673f444c8a362f40f19ffb14d
Source dataset
uspto-grants-1985_05
Patent number
US04518775

Reaction notes

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