Hydrazine hydrate (1:1) → 8-Amino-1,4-diethyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one

HRID 1687335Notes

Reaction equation

HRID 1687335 reaction equation
[CH2:1]([N:3]1[C:9](=[O:10])[C:8]2[CH:11]=[CH:12][C:13]([N+:15]([O-])=O)=[CH:14][C:7]=2[N:6]([CH2:18][CH3:19])[CH2:5][CH2:4]1)[CH3:2].O.NN>[Pd].C(O)C>[NH2:15][C:13]1[CH:12]=[CH:11][C:8]2[C:9](=[O:10])[N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]([CH2:18][CH3:19])[C:7]=2[CH:14]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67264018Diethyl-8-nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one

Product 1

HCID 672633818-Amino-1,4-diethyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-oneYield 102.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of Diethyl-8-nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (25.0 g, 0.095 mol) and 10% palladium on carbon (2.0 g) in ethanol (600 mL) was slowly added hydrazine hydrate (150 mL) and heated to 75° C. for 5 hr. After evaporation, toluene (50 mL) and ethanol (50 mL) were added and distilled leaving 8-Amino-1,4-diethyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one as a yellow solid (22.75 g, 85%). Mp 140-141° C.; LCMS (m/e) 233 (M); 1H-NMR (DMSO, 400 MHz) δ 7.14-7.12 (d, 1H, J=8.85 Hz), 6.10-6.09 (d, 1H, J=6.82 Hz), 5.35 (s, 2H), 3.46-3.41 (q, 2H, 7.07 Hz), 3.19-3.16 (t, 2H, J=5.31 Hz), 3.09-3.03 (q, 2H, J=7.07 Hz), 1.12-1.06 (q, 6H, J=7.07 Hz).

Workup

  1. customAfter evaporation, toluene (50 mL) and ethanol (50 mL)
  2. additionwere added
  3. distillationdistilled

Sources & evidence

ORD record
ord-4a03389345444f2e84ae8d7e6704ed41
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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