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

HRID 1363105Notes

Reaction equation

HRID 1363105 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 cone. HC (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 cone
  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-e2da06d3b5b649abb492ccc92ef7bb63
Source dataset
uspto-grants-2011_02
Patent number
US07884113B2

Reaction notes

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