Ethanol → HCID 67264743, compound

HRID 1040923Notes

Reaction equation

HRID 1040923 reaction equation
[CH:1]([N:4]1[C:10]2[CH:11]=[C:12]([N+:15]([O-])=O)[CH:13]=[CH:14][C:9]=2[C:8](=[O:18])[NH:7][CH2:6][CH2:5]1)([CH3:3])[CH3:2].C(O)C.C(Cl)Cl>[Pd].CO>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]2[C:8](=[O:18])[NH:7][CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[C:10]=2[CH:11]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 6344DichloromethaneHCID 67263295HCID 67263295, compound

Product 1

HCID 67264743HCID 67264743, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a 500 ml round bottom flask, 1-isopropyl-8-nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (4.10 g, 16 mmoles), ethanol (300 ml), and palladium (320 mg) were added. The mixture was evacuated and charged with hydrogen (3 times). The reaction was stirred at room temperature under hydrogen balloon for the weekend (64 hrs). The solid was filtered through celite and washed with methanol. The solvent was then removed under vacuum to afford a brown oil. The desired product (2.15 g, 60% yield) was isolated via column chromatography with DCM and methanol as eluant (0 to 25% methanol). NMR 1H-(DMSO)-δ-7.32-7.52 (m, 1H), 7.00 (bs, 1H), 6.80 (bs, 1H), 4.80 (p, 1H), 3.40 (bs, 4H), 1.10 (d, 6H, J=6.58 Hz)

Workup

  1. customThe mixture was evacuated
  2. additioncharged with hydrogen (3 times)
  3. filtrationThe solid was filtered through celite
  4. washwashed with methanol
  5. customThe solvent was then removed under vacuum
  6. customto afford a brown oil

Sources & evidence

ORD record
ord-a4e0f542c41647e4b7a485c6529451a0
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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