Sodium Carbonate → HCID 18470625, compound

HRID 2228499Notes

Reaction equation

[CH:1]1(Br)[CH2:4][CH2:3][CH2:2]1.[CH3:6][O:7][C:8]1[C:9]([OH:23])=[C:10]([C:15]([N+:20]([O-:22])=[O:21])=[CH:16][C:17]=1[O:18][CH3:19])[C:11]([O:13][CH3:14])=[O:12].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH:1]1([O:23][C:9]2[C:8]([O:7][CH3:6])=[C:17]([O:18][CH3:19])[CH:16]=[C:15]([N+:20]([O-:22])=[O:21])[C:10]=2[C:11]([O:13][CH3:14])=[O:12])[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 100 °C

Procedure

Cyclobutyl bromide (0.44 ml, 0.0047 mol) was added to a suspension of methyl 3,4-dimethoxy-2-hydroxy-6-nitrobenzoate (1 g, 0.0039 mol) and potassium carbonate (1.2 g, 0.0086 mol) in dimethylformamide (10 ml) and the reaction stirred at 100° C. for 4 hours. On cooling, aqueous sodium carbonate solution was added and the mixture extracted with ethyl acetate (2×40 ml). The combined organic extracts were washed with water, dried (MgSO4), filtered and evaporated under reduced pressure. The crude product was purified on silica gel eluting with diethyl ether to give the subtitle compound as a colourless oil (511 mg, 42%). Rf 0.89 (diethyl ether). MS m/z 312 (MH)+. 1H-NMR (CDCl3): Γ=1.48 (1H, m), 1.76(1H, m), 2.27 (4H, m), 2.94(9H, m), 4.70(1H, m), 7.51 (1H, s).

Workup

temperatureOn cooling
extractionthe mixture extracted with ethyl acetate (2×40 ml)
washThe combined organic extracts were washed with water
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated under reduced pressure
customThe crude product was purified on silica gel eluting with diethyl ether

Sources & evidence

ORD record: ord-d90c055e1ed342cb8edc327a02efa220
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06417194B1

Reaction notes

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