Ammonium formate → 7-Amino-8-isopropoxy-1-methyl-1,3,4,5-tetrahydro-2H-benzo[B]azepin-2-one

HRID 518886Notes

Reaction equation

HRID 518886 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[C:10]([O:16][CH:17]([CH3:19])[CH3:18])[C:11]([N+:13]([O-])=O)=[CH:12][C:7]=2[CH2:6][CH2:5][CH2:4][C:3]1=[O:20].C([O-])=O.[NH4+]>[Pd].CO>[NH2:13][C:11]1[C:10]([O:16][CH:17]([CH3:19])[CH3:18])=[CH:9][C:8]2[N:2]([CH3:1])[C:3](=[O:20])[CH2:4][CH2:5][CH2:6][C:7]=2[CH:12]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 866980321-methyl-7-nitro-8-(propan-2-yloxy)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Product 1

HCID 866980337-Amino-8-isopropoxy-1-methyl-1,3,4,5-tetrahydro-2H-benzo[B]azepin-2-oneYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

In a microwave tube, 316 mg of 1-methyl-7-nitro-8-(propan-2-yloxy)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one are introduced into 20 ml of methanol. 443 mg of ammonium formate and 363 mg of Pd/C (10%) are added. The reaction medium is microwave-heated at 80° C. for 5 minutes. The mixture is filtered on Clarcel and the Clarcel is rinsed with methanol. The filtrate is concentrated under reduced pressure, so as to obtain 280 mg of 7-amino-1-methyl-8-(propan-2-yloxy)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in the form of a colourless gum.

Workup

  1. filtrationThe mixture is filtered on Clarcel
  2. washthe Clarcel is rinsed with methanol
  3. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-c944b4fe4ac5451c9e961172dd6de338
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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