1,3-Diethyl-8-methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[d]azepin-2-one → 7-Amino-1,3-diethyl-8-methoxy-1,3,4,5-tetrahydro-3-benzazepin-2-one

HRID 1686974Notes

Reaction equation

HRID 1686974 reaction equation
[CH2:1]([CH:3]1[C:9]2[CH:10]=[C:11]([O:17][CH3:18])[C:12]([N+:14]([O-])=O)=[CH:13][C:8]=2[CH2:7][CH2:6][N:5]([CH2:19][CH3:20])[C:4]1=[O:21])[CH3:2].[H][H]>[Pd].CCO>[NH2:14][C:12]1[C:11]([O:17][CH3:18])=[CH:10][C:9]2[CH:3]([CH2:1][CH3:2])[C:4](=[O:21])[N:5]([CH2:19][CH3:20])[CH2:6][CH2:7][C:8]=2[CH:13]=1

Participants

5

Reactant 2

HCID 672642751,3-Diethyl-8-methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[d]azepin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 672644667-Amino-1,3-diethyl-8-methoxy-1,3,4,5-tetrahydro-3-benzazepin-2-oneYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1,3-Diethyl-8-methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[d]azepin-2-one (205 mg, 0.70 mmol) was charged to 10 ml EtOH in a Parr bottle and then 50 mg of 10% Pd/C was also charged. The resulting suspension was shaken under 40 psi hydrogen (g) for 2 h. The resulting suspension was filtered through celite and evaporated to yield 7-amino-1,3-diethyl-8-methoxy-1,3,4,5-tetrahydro-3-benzazepin-2-one (170 mg, 93%) which was used crude in the next reaction. 1H-NMR (CDCl3) δ 6.58 (s, 1H), 6.44 (s, 1H), 3.92-3.77 (m, 5H), 3.70-3.40 (br s, 1H), 3.58-3.38 (m, 3H), 3.09 (p, J=7 Hz, 1H), 2.95 (p, J=7 Hz, 1H), 2.20 (p, J=7 Hz, 1H), 1.90 (p, J=7 Hz, 1H), 1.10 (t, J=7 Hz, 3H), 1.04 (t, J=7 Hz, 3H); LC/Ms (ESI+): 263 (M+H).

Workup

  1. filtrationThe resulting suspension was filtered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-92df43edecb948a7a5a8e0f9bbb27b8a
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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