4-Chloro-2-nitro-DL-phenylalanine → 3-Amino-7-chloro-3,4-dihydroquinolin-2(1H)-one

HRID 1643886Notes

Reaction equation

HRID 1643886 reaction equation
[NH2:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[N+:14]([O-])=O)[C:3](O)=[O:4]>CCO.[Pt]>[NH2:1][CH:2]1[CH2:6][C:7]2[C:8](=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=2)[NH:14][C:3]1=[O:4]

Participants

4

Reactant 1

HCID 122325564-Chloro-2-nitro-DL-phenylalanine

Product 1

HCID 122325703-Amino-7-chloro-3,4-dihydroquinolin-2(1H)-oneYield 54.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 152A (1.0 g, 4.1 mmol) in 50% aqueous EtOH (40 mL), 10% Pt/C (100 mg) was added under argon and the mixture was hydrogenated at 35 psi for 1 h. The reaction mixture was filtered via a pad of celite and the filtrate was concentrated. The residue was dissolved in conc. HCl (10 mL) and stirred at RT for 6 h. The mixture was then concentrated and dissolved in 100 mL of saturated aqueous sodium bicarbonate. The white solid was filtered and dried to afford 0.44 g of 152B.

Workup

  1. filtrationThe reaction mixture was filtered via a pad of celite
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in conc. HCl (10 mL)
  4. concentrationThe mixture was then concentrated
  5. dissolutiondissolved in 100 mL of saturated aqueous sodium bicarbonate
  6. filtrationThe white solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-73817635f3084761a5dd97591a1602b5
Source dataset
uspto-grants-2012_02
Patent number
US08119808B2

Reaction notes

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