Nitroethane → HCID 69621553, compound

HRID 1790288Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[CH:15]=O.C([O-])(=O)C.[NH4+].[N+:22]([CH2:25][CH3:26])([O-:24])=[O:23]>>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[CH:15]=[C:25]([N+:22]([O-:24])=[O:23])[CH3:26]

Participants

Reactant 3

HCID 6587Nitroethane

HCID 517165Ammonium Acetate

HCID 105848151,4-Dimethoxy-2-naphthaldehyde

Product 1

HCID 69621553HCID 69621553, compound

Conditions

Temperature: 60 °C

Procedure

To a solution of the product from Step A (0.8 g, 2.93 mmol) in nitroethane (10 mL) was added ammonium acetate (0.45 g, 5.84 mmol). The mixture was stirred at 60° C. overnight. The excess nitroethane was removed and the residue purified by flash chromatography (silica gel, ethyl acetate/hexane: 0.5/9.5) to give 0.5 g of a yellow solid: 1H NMR (DMSO-d6) δ 2.45 (s, 3H, CH3), 3.84 (s, 3H, OCH3), 4.00 (s, 3H, OCH3), 6.95 (s, 1H, Ar—H), 7.65 (m, 2H, Ar—H), 8.10 (m, 2H, Ar—H), 8.29 (s, 1H, CH═).

Workup

customThe excess nitroethane was removed
customthe residue purified by flash chromatography (silica gel, ethyl acetate/hexane: 0.5/9.5)

Sources & evidence

ORD record: ord-376d69b127ad44a48115925c1173cab5
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071225B2

Reaction notes

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