2,2,2-Trifluoro-1-(7-methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone → 1-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-2,2,2-trifluoro-ethanone

HRID 1687052Notes

Reaction equation

HRID 1687052 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([O:19][CH3:20])[C:14]([N+:16]([O-])=O)=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4]>CO.[Pd]>[NH2:16][C:14]1[C:13]([O:19][CH3:20])=[CH:12][C:9]2[CH2:10][CH2:11][N:5]([C:3](=[O:4])[C:2]([F:1])([F:21])[F:22])[CH2:6][CH2:7][C:8]=2[CH:15]=1

Participants

4

Reactant 1

HCID 866338662,2,2-Trifluoro-1-(7-methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone

Product 1

HCID 866338681-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-2,2,2-trifluoro-ethanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2,2,2-trifluoro-1-(7-methoxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone in methanol was added palladium 10% wt on Carbon (50% wet). The mixture was shaken in a Parr apparatus under an atmosphere of Hydrogen (50 PSI) for 30 minutes. Filtration through Celite and evaporation of the solvent provided quantitatively 1-(7-amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-2,2,2-trifluoro-ethanone, which was used without further purification. 1H-NMR (CDCl3; amide rotamers observed) δ 6.58 (1H), 6.53 (1H), 3.83 (s, 3H), 3.15-4.25 (br s, 2H), 3.60-3.78 (4H), 2.79-2.92 (4H); LC/MS (ESI+): 288.99 (M+H).

Workup

  1. filtrationFiltration
  2. customthrough Celite and evaporation of the solvent

Sources & evidence

ORD record
ord-bf9dd34623a240eb870c66f0fddc696e
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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