Sodium Nitrite → HCID 178440468, compound

HRID 14502

Reaction equation

[NH2:1][C:2]1[C:11]([NH2:12])=[C:10]2[C:5]([C:6](=[O:23])[C:7]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[C:8]([CH:13]([CH3:15])[CH3:14])[O:9]2)=[CH:4][CH:3]=1.[N:24]([O-])=O.[Na+]>C(O)(=O)C>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:7]2[C:6](=[O:23])[C:5]3[C:10]([O:9][C:8]=2[CH:13]([CH3:14])[CH3:15])=[C:11]2[N:12]=[N:24][NH:1][C:2]2=[CH:3][CH:4]=3)=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred mixture of 7,8-diamino-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one (115 mg, 0.35 mmol) and 5% aqueous acetic acid (5 ml) is cooled to 0° C., and sodium nitrite (26 mg, 0.38 mmol) is added portionwise. The mixture is stirred for 18 h as it is allowed to warm to room temperature. The reaction is quenched with saturated aqueous sodium bicarbonate (50 ml), and the mixture is extracted with ethyl acetate (3×50 ml). The organic phases are combined, washed with saturated aqueous sodium bicarbonate (50 ml) and then with saturated brine (50 ml), dried (MgSO4), filtered and evaporated under reduced pressure. The residue is purified by chromatography on silica gel using n-hexane/ethyl acetate (0-100% ethyl acetate) as eluant to give the product as a colourless solid.

Workup

temperatureto warm to room temperature
customThe reaction is quenched with saturated aqueous sodium bicarbonate (50 ml)
extractionthe mixture is extracted with ethyl acetate (3×50 ml)
washwashed with saturated aqueous sodium bicarbonate (50 ml)
dry with materialwith saturated brine (50 ml), dried (MgSO4)
filtrationfiltered
customevaporated under reduced pressure
customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record: ord-a81fa0164648473a9dbc87061664acbf
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732435B2

Linked notes

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