Ethanol → HCID 67263964, compound

HRID 1041483Notes

Reaction equation

HRID 1041483 reaction equation
[CH2:1]([N:3]1[C:9]2[CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=[CH:13][C:8]=2[C:7](=[O:17])[N:6]([CH2:18][C:19]([N:21]([CH3:23])[CH3:22])=[O:20])[CH2:5][CH2:4]1)[CH3:2].C(O)C>[Pd]>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]2[C:7](=[O:17])[N:6]([CH2:18][C:19]([N:21]([CH3:22])[CH3:23])=[O:20])[CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 67264446HCID 67264446, compound

Product 1

HCID 67263964HCID 67263964, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Into a Round bottom flask, 2-(1-ethyl-8-nitro-5-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-N,N-dimethyl-acetamide (0.27 g, 0.00084 mol;), Ethanol (20.0 mL, 0.342 mol;) and 10% Pd/C (10:90, Palladium:carbon black, 0.100 g) were added the reaction was evacuated and charged with hydrogen (3 times). The mixture was stirred at room temperature overnight under an atmosphere of Hydrogen via a balloon. The solid was filtered through Celite and washed with EtOH. The solvent was removed under vacuum to give 2-(8-amino-1-ethyl-5-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-N,N-dimethyl-acetamide as a white solid (0.24 g, 98%). LC/MS (ESI+) 291.19 (M+H).

Workup

  1. customwas evacuated
  2. additioncharged with hydrogen (3 times)
  3. filtrationThe solid was filtered through Celite
  4. washwashed with EtOH
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-cdfcccca612a4581915d704528f4e46d
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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