HCID 117777409, compound → HCID 117777424, compound

HRID 928543Notes

Reaction equation

HRID 928543 reaction equation
C([O:8][C:9]1[C:10]([N+:26]([O-])=O)=[C:11]([CH:16]=[CH:17][C:18]=1[C:19]1[C:20]([CH3:25])=[N:21][O:22][C:23]=1[CH3:24])[C:12]([O:14][CH3:15])=[O:13])C1C=CC=CC=1>CO>[NH2:26][C:10]1[C:9]([OH:8])=[C:18]([C:19]2[C:20]([CH3:25])=[N:21][O:22][C:23]=2[CH3:24])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

3

Reactant 1

HCID 117777409HCID 117777409, compound

Product 1

HCID 117777424HCID 117777424, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of methyl 3-(benzyloxy)-4-(3,5-dimethylisoxazol-4-yl)-2-nitrobenzoate (0.959 g, 2.51 mmol) in methanol (49.9 mL) was degassed with nitrogen, treated with 10% Pd/C, Degussa type, (0.144 g), and hydrogenated with a balloon of hydrogen for 1 h. A solution formed during the first 30 min. The reaction mixture was filtered through a cartridge and the solids were washed with methanol. The filtrate was concentrated to give the desired product (0.656 g, quantitative) as an orange solid that was used without further purification. LCMS calculated for C13H15N2O4 (M+H)+: m/z=263.1. found: 263.1.

Workup

  1. customwas degassed with nitrogen
  2. additiontreated with 10% Pd/C, Degussa type, (0.144 g), and hydrogenated with a balloon of hydrogen for 1 h
  3. customA solution formed during the first 30 min
  4. filtrationThe reaction mixture was filtered through a cartridge
  5. washthe solids were washed with methanol
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-005423255ce4478dadb26b733e2e9242
Source dataset
uspto-grants-2016_03
Patent number
US09290514B2

Reaction notes

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