HCID 10014501, compound → 3-(Hydroxymethyl)-3,4-dihydroquinoxalin-2(1H)-one

HRID 1378771Notes

Reaction equation

HRID 1378771 reaction equation
C[O:2][C:3](=O)[CH:4]([CH2:15][OH:16])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O>[Pd].CO>[OH:2][CH2:3][CH:4]1[NH:5][C:6]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:12][C:15]1=[O:16]

Participants

4

Reactant 1

HCID 10014501HCID 10014501, compound

Product 1

HCID 103298813-(Hydroxymethyl)-3,4-dihydroquinoxalin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-(2-nitrophenyl)-DL-serine methyl ester (XI, EXAMPLE 286, 0.506 g, 4.30 g), palladium on carbon (10%, 506 g) and 150 ml of methanol is shaken under hydrogen at 40 psi for 3.5 hr. The catalyst is then removed by filtration and the filtrate is concentrated under reduced pressure. The residue is then chromatographed on silica gel (400 ml) using eluting with methanol/methylene chloride (6/94), the appropriate fractions are pooled and concentrated to give the title compound, NMR (CDCl3) 2.70, 3.90, 4.00-4.18, 6.75, 6.92, 8.23. δ.

Workup

  1. customThe catalyst is then removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is then chromatographed on silica gel (400 ml)
  4. washusing eluting with methanol/methylene chloride (6/94)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-25cde7d10bd346f2b9d36a9ea8902a5f
Source dataset
uspto-grants-1997_09
Patent number
US05668282

Reaction notes

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