3-Nitro-5-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)pyridin-2-amine dihydrochloride → 5-(2,3,4,5-Tetrahydro-1,4-benzoxazepin-7-yl)pyridine-2,3-diamine dihydrochloride

HRID 241230Notes

Reaction equation

HRID 241230 reaction equation
[ClH:1].Cl.[N+:3]([C:6]1[C:7]([NH2:23])=[N:8][CH:9]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]3[O:21][CH2:20][CH2:19][NH:18][CH2:17][C:16]=3[CH:22]=2)[CH:11]=1)([O-])=O>C(O)(=O)C.C(O)C.[Pd]>[ClH:1].[ClH:1].[O:21]1[C:15]2[CH:14]=[CH:13][C:12]([C:10]3[CH:11]=[C:6]([NH2:3])[C:7]([NH2:23])=[N:8][CH:9]=3)=[CH:22][C:16]=2[CH2:17][NH:18][CH2:19][CH2:20]1

Participants

5

Reactant 1

HCID 668206213-Nitro-5-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)pyridin-2-amine dihydrochloride

Product 1

HCID 668208225-(2,3,4,5-Tetrahydro-1,4-benzoxazepin-7-yl)pyridine-2,3-diamine dihydrochlorideYield 199.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 3-nitro-5-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)pyridin-2-amine dihydrochloride (1.0 g, 2.8 mmol) in acetic acid (20 mL) and ethanol (20 mL) was added Pd/C (10% wt/wt, 0.5 g) and the reaction mixture was stirred under H2 (45 PSI) for 1 hour. The resulting pale yellow solution was filtered through Celite and the filtrate was concentrated to give 5-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)pyridine-2,3-diamine dihydrochloride (0.92 g, 100%) as a yellow powder. MS (EI) for C14H16N4O: 257.3 (MH+).

Workup

  1. filtrationThe resulting pale yellow solution was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4abdc7aff986484d87876a810bea9265
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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