Hydrochloric Acid → 2-Nitro-4-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)aniline dihydrochloride

HRID 241213Notes

Reaction equation

HRID 241213 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][C:12]=3[CH:25]=2)=[CH:4][C:3]=1[N+:26]([O-:28])=[O:27].[ClH:29]>O1CCOCC1>[ClH:29].[ClH:29].[N+:26]([C:3]1[CH:4]=[C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][NH:14][CH2:13][C:12]=3[CH:25]=2)[CH:6]=[CH:7][C:2]=1[NH2:1])([O-:28])=[O:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 675056591,1-dimethylethyl 7-(4-amino-3-nitrophenyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Product 1

HCID 668203152-Nitro-4-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)aniline dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 1,1-dimethylethyl 7-(4-amino-3-nitrophenyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (10 g, 26 mmol) in dioxane (50 mL) was added hydrogen chloride in dioxane (4 M, 50 mL, 200 mmol), and the mixture was stirred at rt for 16 h. The volatile materials were then removed to provide 2-nitro-4-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)aniline dihydrochloride in quantitative yield. MS (EI) for C15H15N3O3: 286 (MH+).

Workup

  1. customThe volatile materials were then removed

Sources & evidence

ORD record
ord-4214301b3c3445f8b7c602e80e20eeac
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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