7,8,9,10-Tetrahydro-8-methyl-2,3-bis(phenylmethoxy)-pyrido[4,3-f]quinoxalin-6-yl phosphonic acid diethyl ester → 1,2,3,4,7,8,9,10-Octahydro-8-methyl-2,3-dioxopyrido[4,3-f]quinoxalin-6-yl phoshonic acid diethyl ester

HRID 48246Notes

Reaction equation

HRID 48246 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[C:10]2[CH2:38][N:37]([CH3:39])[CH2:36][CH2:35][C:11]=2[C:12]2[N:13]=[C:14]([O:27]CC3C=CC=CC=3)[C:15]([O:19]CC3C=CC=CC=3)=[N:16][C:17]=2[CH:18]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]>C(O)(=O)C.[Pd]>[CH2:6]([O:5][P:4]([C:9]1[C:10]2[CH2:38][N:37]([CH3:39])[CH2:36][CH2:35][C:11]=2[C:12]2[NH:13][C:14](=[O:27])[C:15](=[O:19])[NH:16][C:17]=2[CH:18]=1)(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

4

Reactant 1

HCID 231936707,8,9,10-Tetrahydro-8-methyl-2,3-bis(phenylmethoxy)-pyrido[4,3-f]quinoxalin-6-yl phosphonic acid diethyl ester

Product 1

HCID 231936831,2,3,4,7,8,9,10-Octahydro-8-methyl-2,3-dioxopyrido[4,3-f]quinoxalin-6-yl phoshonic acid diethyl esterYield 83.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 23938PalladiumSolvent

Procedure

A solution of the compound from Example 105 (0.34 g, 0.65 mmol) was dissolved in 60 mL of acetic acid and hydrogenated at 52 psi over 20% Pd/C. The reaction mixture was filtered and concentrated. The residue was dissolved in EtOH (3 mL) and concentrated. This procedure was repeated several times. The residue was then dissolved in EtOH and triturated with ethyl acetate. The solid which formed was collected by suction filtration and dried under vacuum to give the title compound as a yellow solid (0.20 g, 83% yield) mp 310-330° C. (dec).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOH (3 mL)
  4. concentrationconcentrated
  5. dissolutionThe residue was then dissolved in EtOH
  6. customtriturated with ethyl acetate
  7. customThe solid which formed
  8. filtrationwas collected by suction filtration
  9. customdried under vacuum

Sources & evidence

ORD record
ord-9322d0d46fa741b8997da5a7a5c5355d
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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