1-Isopropyl-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one → 7-Amino-1-isopropyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

HRID 1040999Notes

Reaction equation

HRID 1040999 reaction equation
[CH:1]([N:4]1[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:6]2[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:5]1=2)([CH3:3])[CH3:2].[H][H]>[Pd].C(O)C>[NH2:16][C:13]1[CH:14]=[CH:15][C:5]2[N:4]([CH:1]([CH3:3])[CH3:2])[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:6]=2[CH:12]=1

Participants

5

Reactant 2

HCID 672639191-Isopropyl-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 672642257-Amino-1-isopropyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-oneYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-Isopropyl-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (474 mg, 1.91 mmol) was charged to 10 ml ethanol and 100-200 mg 10% palladium on carbon was added. The suspension was hydrogenated at 30 psi hydrogen for 2.5 hours and followed by NMR. The reaction was filtered through a ¼″ pad of celite and the pad washed with 4×10 ml portions of methanol. The resulting solution was clarified through a 45 micron frit to yield 7-Amino-1-isopropyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (346 mg, 83% yield) as a clear oil. 1H-NMR (CDCl3) δ 6.96 (d, J=8.3 Hz, 1H), 6.56 (d, J=8.3 Hz, 1H), 6.51 (s, 1H), 4.80 (m, 1H), 3.67 (br s, 1H), 2.71 (m, 1H), 2.44 (m, 1H), 2.20 (m, 3H), 1.84 (m, 1H), 1.36 (d, J=6.8 Hz, 3H), 1.01 (d, J=6.8 Hz, 3H). LC/MS (ESI+)=219 (M+H).

Workup

  1. additionwas added
  2. filtrationThe reaction was filtered through a ¼″ pad of celite
  3. washthe pad washed with 4×10 ml portions of methanol

Sources & evidence

ORD record
ord-6773b46169124d108ff796abd10f7433
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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