HCID 67263944, compound → HCID 67263851, compound

HRID 1687965Notes

Reaction equation

HRID 1687965 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:17]([O-])=O)=[CH:5][C:6]2[C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][C:9](=[O:15])[NH:8][C:7]=2[CH:16]=1>CO.[Pd]>[NH2:17][C:4]1[C:3]([O:2][CH3:1])=[CH:16][C:7]2[NH:8][C:9](=[O:15])[CH2:10][CH2:11][C:12]([CH3:14])([CH3:13])[C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 67263944HCID 67263944, compound

Product 1

HCID 67263851HCID 67263851, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

8-Methoxy-5,5-dimethyl-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (160 mg, 0.60 mmol) was hydrogenated in the presence of 10% Pd/C, 50% wet (80 mg) in Methanol (15 mL) overnight (balloon). Conc. of the filtered reaction afforded 7-Amino-8-methoxy-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (122 mg, 86%), which was used without purification. 1H-NMR (CDCl3): 6.94 (s, 1H), 6.76 (s, 1H), 6.38 (s, 1H), 3.85 (s, 3H), 3.76 (s, 2H), 2.35 (t, 2H, J=7.0 Hz), 2.07 (t, 2H, J=7.0 Hz), 1.37 (s, 6H).

Workup

  1. customConc. of the filtered reaction

Sources & evidence

ORD record
ord-c27b7d606c8446b3a1ae50e43a666024
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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