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

HRID 1465112Notes

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-2292b416fbd644d7a88a49252ac1755e
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999976B2

Reaction notes

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