Ammonium Chloride → 2-(2-Aminophenyl)-n-(6-chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)acetamide

HRID 452251Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[O:11][C:7]1([CH2:10][CH2:9][CH2:8]1)[CH2:6][CH:5]2[NH:15][C:16](=[O:27])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-])=O.[NH4+].[Cl-]>C(O)C.O.[Fe]>[NH2:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][C:16]([NH:15][CH:5]1[C:4]2[C:12](=[CH:13][CH:14]=[C:2]([Cl:1])[CH:3]=2)[O:11][C:7]2([CH2:10][CH2:9][CH2:8]2)[CH2:6]1)=[O:27]

Participants

Conditions

Temperature: 80 °C

Procedure

To a well stirred solution of step 1 intermediate (200 mg, 0.512 mmol) in ethanol (5 ml) was added NH4Cl (276 mg, 5.102 mmol) in water (3 ml) at room temperature. The reaction mixture was stirred for 15 min at the same temperature and then heated to 80° C. for 15 min. Iron (86 mg, 1.552 mmol) was added at that same temperature. The reaction mixture was refluxed further for 2 h. The residue obtained after the evaporation of the solvent was extracted with chloroform (2×50 ml). This chloroform layer was passed through celite. The layers were separated. Organic layers were washed with water (2×30 ml), brine (30 ml) and dried over Na2SO4. Solvent was evaporated to give 150 mg of the product.

Workup

temperatureThe reaction mixture was refluxed further for 2 h
customThe residue obtained
customafter the evaporation of the solvent
extractionwas extracted with chloroform (2×50 ml)
customThe layers were separated
washOrganic layers were washed with water (2×30 ml), brine (30 ml)
dry with materialdried over Na2SO4
customSolvent was evaporated

Sources & evidence

ORD record: ord-62fe4c6ec0f547baad737a0d59e230aa
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487121B2

Reaction notes

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