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

HRID 473872Notes

Reaction equation

HRID 473872 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].CO.[ClH:31]>O1CCOCC1.C(OCC)C>[ClH:31].[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 675056591,1-dimethylethyl 7-(4-amino-3-nitrophenyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Product 1

HCID 675138822-Nitro-4-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)aniline hydrochloride saltYield 72%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-dimethylethyl 7-(4-amino-3-nitrophenyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (example 8, step 1) (6.0 g, 15.6 mmol) was taken into warm methanol (50 mL) followed by addition of 4M hydrogen chloride in dioxane (50 mL) in portions and the warm solution was allowed to slowly cool to room temperature over 1 h. The mixture was diluted with ethyl ether (100 mL) and the yellow solid was collected by filtration and dried to give 2-nitro-4-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)aniline hydrochloride salt (3.61 g, 72% yield) as a yellow solid. 1H NMR (400 MHz, D2O): 7.79 (s, 1H), 7.44 (d, 1H), 7.29 (s, 1H), 7.26 (d, 1H), 7.02 (d, 1H), 6.82 (d, 1H), 4.34 (s, 2H), 4.32 (br m, 2H), 3.67 (br m, 2H).

Workup

  1. filtrationthe yellow solid was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-52dfc59403a045cfb036461d538417c9
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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