3-{[(Benzyloxy)carbonyl]amino}-7-vinylquinoline-2-carboxylic acid → 3-Amino-7-ethylquinoline-2-carboxylic acid

HRID 924418Notes

Reaction equation

HRID 924418 reaction equation
C(OC([NH:11][C:12]1[C:13]([C:24]([OH:26])=[O:25])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([CH:22]=[CH2:23])[CH:16]=2)=O)C1C=CC=CC=1.[H][H]>CO.[Pd]>[NH2:11][C:12]1[C:13]([C:24]([OH:26])=[O:25])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([CH2:22][CH3:23])[CH:16]=2

Participants

5

Reactant 2

HCID 867268683-{[(Benzyloxy)carbonyl]amino}-7-vinylquinoline-2-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 867268773-Amino-7-ethylquinoline-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-{[(benzyloxy)carbonyl]amino}-7-vinylquinoline-2-carboxylic acid (673.9 mg, 1.934 mmol) in MeOH (25.0 mL) was added 10 wt % Pd on carbon (100.1 mg, 0.09406 mmol). The mixture was stirred at room temperature hydrogen (1 atm) for 15 h. The reaction mixture was filtered through a pad of diatomaceous earth (eluted with MeOH) and then concentrated under reduced pressure. The resulting crude sub-title compound was used directly in the next step residue without further purification (380.6 mg, 91%). LCMS calc. for C12H13N2O2 (M+H)+: m/z=217.1. found 217.0.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth (eluted with MeOH)
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting crude sub-title compound was used directly in the next step residue without further purification (380.6 mg, 91%)

Sources & evidence

ORD record
ord-62c9d41a0767491ca0249d2fac3af663
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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