Hydrochloric Acid → HCID 18399742, compound

HRID 1018997Notes

Reaction equation

HRID 1018997 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:20]([N+:21]([O-])=O)=[C:19]([CH2:24][C:25]#[N:26])[CH:18]=[CH:17][N:16]=2)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>[Fe].C(O)C>[CH2:2]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:20]([NH2:21])=[C:19]([CH2:24][C:25]#[N:26])[CH:18]=[CH:17][N:16]=2)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18399759HCID 18399759, compound

Product 1

HCID 18399742HCID 18399742, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

43 ml of hydrochloric acid and 35 g of iron powder are added to a suspension, that has been heated at 80° C. for 1 hour, of 59 mmol of the product obtained in Step A in 1.5 1 of absolute ethanol. After 2 hours 30 minutes at 80° C., filtration while hot, and concentration of the reaction mixture under reduced pressure, the residue is taken up in water, rendered basic with a 20% sodium hydroxide solution and extracted with ethyl acetate. The organic phase is subsequently dried, filtered and evaporated, and chromatography of the residue on silica gel (dichloromethane/ethanol: 90/10) enables the expected product to be isolated.

Workup

  1. filtrationfiltration while hot, and concentration of the reaction mixture under reduced pressure
  2. extractionextracted with ethyl acetate
  3. customThe organic phase is subsequently dried
  4. filtrationfiltered
  5. customevaporated
  6. customto be isolated

Sources & evidence

ORD record
ord-c6ad296d9e17459796d1805f29bffb80
Source dataset
uspto-grants-2002_11
Patent number
US06486171B2

Reaction notes

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