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

HRID 1736713Notes

Reaction equation

HRID 1736713 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-28833d30657348578d34a8550cb670e9
Source dataset
uspto-grants-1996_07
Patent number
US05541324

Reaction notes

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