Hydrazine hydrate (1:1) → 7-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

HRID 1687172Notes

Reaction equation

HRID 1687172 reaction equation
O.NN.[CH3:4][C:5]1([CH3:20])[CH2:11][CH2:10][C:9](=[O:12])[NH:8][C:7]2[CH:13]=[CH:14][C:15]([N+:17]([O-])=O)=[CH:16][C:6]1=2>[Pd].C(O)C>[NH2:17][C:15]1[CH:14]=[CH:13][C:7]2[NH:8][C:9](=[O:12])[CH2:10][CH2:11][C:5]([CH3:20])([CH3:4])[C:6]=2[CH:16]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 578538385,5-Dimethyl-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

Product 1

HCID 578538307-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Added 13 mL of ethanol, 10% Palladium on activated carbon (62 mg), and hydrazine monohydrate (171 ul) to 5,5-Dimethyl-7-nitro-1,3,4,5-tetrahydrobenzo[b]azepin-2-one (206 mg, 0.8793 mmol). Heated reaction to 60° C. overnight. Filtered reaction through Celite, and purified by normal phase silica gel chromatography eluting with 90/10/1 CH2Cl2/MeOH/NH4OH to obtain an off-white solid to yield 7-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one. mp 168° C.; LCMS: m/z=205.12 (M+H+), 1H NMR (400 MHz, CDCl3) δ 8.35 (br s, 1H), 6.78 (d, 1H, J=8.3 Hz), 6.72 (s, 1H), 6.54 (d, 1H, J=8.3 Hz), 3.76 (br s, 2H), 2.32 (m, 2H), 2.06 (m, 2H), 1.35 (s, 6H).

Workup

  1. temperatureHeated
  2. customreaction to 60° C. overnight
  3. filtrationFiltered
  4. customreaction through Celite
  5. custompurified by normal phase silica gel chromatography
  6. washeluting with 90/10/1 CH2Cl2/MeOH/NH4OH
  7. customto obtain an off-white solid

Sources & evidence

ORD record
ord-bd884e2aa8b140429fe1c9e89fff3c69
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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