Sodium Carbonate → 5-Amino-4-(3-(dimethylamino)prop-1-ynyl)-2-methylphenyl methyl carbonate

HRID 383376Notes

Reaction equation

[C:1](=[O:21])([O:19][CH3:20])[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([C:12]#[C:13][CH2:14][N:15]([CH3:17])[CH3:16])=[CH:5][C:4]=1[CH3:18].C([O-])([O-])=O.[Na+].[Na+]>C(O)C.C(O)(=O)C.O.[Fe]>[C:1](=[O:21])([O:19][CH3:20])[O:2][C:3]1[CH:8]=[C:7]([NH2:9])[C:6]([C:12]#[C:13][CH2:14][N:15]([CH3:17])[CH3:16])=[CH:5][C:4]=1[CH3:18]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(3-(dimethylamino)prop-1-ynyl)-2-methyl-5-nitrophenyl methyl carbonate (120 mg; 0.41 mmol) in ethanol (2.7 mL) and glacial acetic acid (1.5 mL) was added Fe (92 mg, 1.64 mmol). The mixture was heated at 60° C. for 1 h and then cooled to room temperature. The mixture was diluted with water and carefully neutralized with solid Na2CO3. The resulting solution was extracted with ethyl acetate. The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel chromatography (0-20% ethyl acetate/hexanes) to provide 5-amino-4-(3-(dimethylamino)prop-1-ynyl)-2-methylphenyl methyl carbonate (85 mg, 79% yield). LC/MS m/z 218.3 [M+H]+.

Workup

temperaturecooled to room temperature
extractionThe resulting solution was extracted with ethyl acetate
dry with materialThe combined organic extracts were dried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography (0-20% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-dcc665f0117848008743237b524665ea
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367660B2

Reaction notes

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