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

HRID 518846Notes

Reaction equation

C([O-])=O.[NH4+].[CH3:5][N:6]1[C:12]2[CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][CH2:8][C:7]1=[O:20]>CO.[Pd]>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]2[CH2:10][CH2:9][CH2:8][C:7](=[O:20])[N:6]([CH3:5])[C:12]=2[CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

696 mg of ammonium formate and 581 mg of Pd/C (10%) are added to a solution of 405 mg of 1-methyl-8-nitro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in 39 ml of methanol. 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 give 422 mg of 8-amino-1-methyl-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in the form of a colourless gum.

Workup

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

Sources & evidence

ORD record: ord-b4e73b92b87b486bb4479a159ee8cb3a
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115140B2

Reaction notes

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