HCID 135489139, compound → HCID 135421239, compound

HRID 2053437Notes

Reaction equation

HRID 2053437 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[C:8](=[O:26])[NH:9][C:10]3[C:15]([C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][C:13]([N+:23]([O-])=O)=[CH:12][CH:11]=3)[O:4][N:3]=1>[Pd].CO>[NH2:23][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:26])[C:7]([C:5]1[O:4][N:3]=[C:2]([CH3:1])[CH:6]=1)=[C:16]2[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 135489139HCID 135489139, compound

Product 1

HCID 135421239HCID 135421239, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A flask charged with 3-(3-methyl-isoxazol-5-yl)-6-nitro-4-phenyl-1H-quinolin-2-one (0.2 g, 0.58 mmol)(Example 51), 50 mg of 10% Pd/C, and 10 mL of methanol was shaken on a Parr apparatus under 15 PSI of H2 for 8 hrs. The solution was filtered and concentrated to give 0.18 g (100%) of the title compound as a white solid. 1H NMR (400 MHz, CD3OD) δ 7.44 (m, 3H), 7.22 (m, 3H), 7.04 (m, 1H), 6.50 (m, 1H), 6.34 (s, 1H), 2.20 (s, 3H). Mass spectrum (ESI, m/z) calcd. for C19H15N3O2 317.1, found 318.1 (M+H).

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7f265c06cab742fd9dbae21050c8445a
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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