HCID 86634185, compound → HCID 68631193, compound

HRID 1928864Notes

Reaction equation

HRID 1928864 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:11]2[C:12](=[N:15]O)[CH2:13][O:14][C:10]=2[CH:9]=[CH:8][CH:7]=1>CO.O1CCCC1.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:11]2[CH:12]([NH2:15])[CH2:13][O:14][C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 1

HCID 86634185HCID 86634185, compound

Product 1

HCID 68631193HCID 68631193, compoundYield 109.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the above described 4-(2-methoxy-ethoxy)-benzofuran-3-one oxime (1.19 g, 5 mmol) in methanol (100 mL) and tetrahydrofuran (100 mL) with 10% palladium on carbon (1.42 g) was hydrogenated at 23° C. and atmospheric pressure for 5 days. Filtered the catalyst off, washed with tetrahydrofuran, evaporated the filtrate totally and dried in high vacuum to give the title compound as a red oil (1.15 g, 90%, ca. 90% purity, contains residual starting material); MS: m/e=193.1 (M−NH2+H+).

Workup

  1. additionA mixture of the
  2. customwas hydrogenated at 23° C.
  3. filtrationFiltered the catalyst off,
  4. washwashed with tetrahydrofuran
  5. customevaporated the filtrate totally
  6. customdried in high vacuum

Sources & evidence

ORD record
ord-900aceb62b794740bb94796089528cc9
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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