2-nitro-4-tert-butyl-N-(2-oxo-ethyl)-benzamide → 8-tert-Butyl-2-methoxy-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one

HRID 1879671Notes

Reaction equation

HRID 1879671 reaction equation
[N+:1]([C:4]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[CH:12][C:5]=1[C:6]([NH:8][CH2:9][CH:10]=[O:11])=[O:7])([O-])=O.[C:20](C1C=CC2C(=O)NCC=NC=2C=1)(C)(C)C>CO.[Pd]>[C:16]([C:14]1[CH:13]=[CH:12][C:5]2[C:6](=[O:7])[NH:8][CH2:9][CH:10]([O:11][CH3:20])[NH:1][C:4]=2[CH:15]=1)([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 2

HCID 595485272-nitro-4-tert-butyl-N-(2-oxo-ethyl)-benzamideHCID 667720198-tert-Butyl-3,4-dihydro-benzo[e][1,4]diazepin-5-one

Product 1

HCID 595485398-tert-Butyl-2-methoxy-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

70 mg 10 wt % Pd on carbon was wetted with a small amount of methanol under argon. To this was added 717 mg (3 mmol) 2-nitro-4-tert-butyl-N-(2-oxo-ethyl)-benzamide dissolved in 20 mL methanol. The flask was evacuated and the atmosphere replaced with hydrogen gas using a balloon as ballast, and the mixture was hydrogenated for 3 hours. The reaction was filtered through celite under argon, the celite washed with ethyl acetate. Solvent was removed under vacuum to give a solid. NMR and LC/MS shows this to be a mixture of the title compound and 8-tert-Butyl-3,4-dihydro-benzo[e][1,4]diazepin-5-one as a one to one mixture, which was used without purification.

Workup

  1. customThe flask was evacuated
  2. filtrationThe reaction was filtered through celite under argon
  3. washthe celite washed with ethyl acetate
  4. customSolvent was removed under vacuum
  5. customto give a solid

Sources & evidence

ORD record
ord-eff5da4c4f2f45f6a6d0eb62fe26d7aa
Source dataset
uspto-grants-2012_11
Patent number
US08318719B2

Reaction notes

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