Tetrahydrofuran → HCID 67404328, compound

HRID 906098Notes

Reaction equation

HRID 906098 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[C:3]=1[N+:12]([O-:14])=[O:13].O1CCC[CH2:16]1.C[Si](C=[N+]=[N-])(C)C>CO>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:16])=[O:7])=[C:4]([CH3:11])[C:3]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 167693TrimethylsilyldiazomethaneHCID 53406085HCID 53406085, compound

Product 1

HCID 67404328HCID 67404328, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Amino-2-methyl-3-nitrobenzoic acid (1.87 g, 9.54 mmol) was solubilized in methanol (100 mL) and tetrahydrofuran (100 mL) and was treated with (trimethylsilyl)diazomethane solution (5.3 mL, 10.5 mmol, 2.0M in diethyl ether). After the reaction was shown to be complete, the mixture was concentrated and the residue was purified via column chromatography (silica gel, 5:1 hexanes/ethyl acetate) to give 1.10 g (55% yield) of methyl 4-amino-2-methyl-3-nitrobenzoate. 1H NMR (400 MHz, d6-DMSO): 7.73 (d, 1H), 6.75 (d, 1H), 6.51 (broad s, 2H), 3.75 (s, 3H), 2.37 (s, 3H). MS (EI) for C9H10N2O4: 210 (MH+).

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified via column chromatography (silica gel, 5:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-d352edf749c441fab6153364f6edaa18
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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