Hydrochloric Acid → HCID 18401486, compound

HRID 1018450Notes

Reaction equation

HRID 1018450 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](O)=O)=[C:4]([C:12](=[O:22])[C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[CH:3]=1.O.NN.Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:8][CH2:9][O:22][CH:12]2[C:13]2[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 53668750HCID 53668750, compound

Product 1

HCID 18401486HCID 18401486, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

17.6 g (55 mM) of 4-chloro-2-(4-nitrobenzoyl)-phenylacetic acid and 8 ml of 85% hydrazine hydrate were refluxed in 340 ml of ethanol for 4 hours. The reaction mixture was cooled, acidified with 115 ml of 1 M hydrochloric acid and evaporated. The residue was mixed with 50 ml of water, the crystals were filtered and dried. The resulting hydrazone derivative was dissolved in 300 ml of anhydrous dichloromethane and treated with a solution of 13.4 g (65 mM) of dicyclohexylcarbodiimide in 210 ml of anhydrous dichloromethane. The reaction mixture was stirred at room temperature overnight, then the precipitated crystals were filtered and washed with dichloromethane.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated
  3. additionThe residue was mixed with 50 ml of water
  4. filtrationthe crystals were filtered
  5. customdried
  6. dissolutionThe resulting hydrazone derivative was dissolved in 300 ml of anhydrous dichloromethane
  7. additiontreated with a solution of 13.4 g (65 mM) of dicyclohexylcarbodiimide in 210 ml of anhydrous dichloromethane
  8. filtrationthe precipitated crystals were filtered
  9. washwashed with dichloromethane

Sources & evidence

ORD record
ord-4405ec58fda44b8e8832ea02d369ca8f
Source dataset
uspto-grants-2002_11
Patent number
US06482819B1

Reaction notes

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