Oxo [(phenylmethyl)(1,2,3,4-tetrahydro-6-nitro-5-quinolinyl)amino]acetic Acid Ethyl Ester → HCID 20633118, compound

HRID 48238Notes

Reaction equation

HRID 48238 reaction equation
C(O[C:4](=[O:28])[C:5](=[O:27])[N:6]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:7]1[C:16]([N+:17]([O-])=O)=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][CH2:11][NH:12]2)C>O1CCCC1.[Ni]>[C:21]1([CH2:20][N:6]2[C:7]3[C:8]4[CH2:9][CH2:10][CH2:11][NH:12][C:13]=4[CH:14]=[CH:15][C:16]=3[NH:17][C:4](=[O:28])[C:5]2=[O:27])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 57199892Oxo [(phenylmethyl)(1,2,3,4-tetrahydro-6-nitro-5-quinolinyl)amino]acetic Acid Ethyl Ester

Product 1

HCID 20633118HCID 20633118, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from Example 92 (0.67 g, 1.7 mmol) in 20 ml tetrahydrofuran was treated with Raney nickel (0.1 g) and stirred under a hydrogen atmosphere (1 atm) for 48 hours. The Raney nickel was removed with a magnet and washed with methanol. The remaining solid was collected by filtration, washed with methanol and then dissolved in 2 N HCl and filtered. The filtrate was neutralized with saturated sodium bicarbonate and the precipitate collected by filtration and dried to give the title compound (0.30 g, 57% yield) mp>300° C.

Workup

  1. customThe Raney nickel was removed with a magnet
  2. washwashed with methanol
  3. filtrationThe remaining solid was collected by filtration
  4. washwashed with methanol
  5. dissolutiondissolved in 2 N HCl
  6. filtrationfiltered
  7. filtrationthe precipitate collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-a06ee9b80e5e4768aef51016348be6f1
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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