Methyl 4-aminobenzoate → HCID 57550196, compound

HRID 1716834Notes

Reaction equation

HRID 1716834 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1.CC(C)([O-])C.[K+]>CS(C)=O>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 12082Methyl 4-aminobenzoateHCID 738951-Fluoro-2-nitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 57550196HCID 57550196, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1-fluoro-2-nitrobenzene (0.46 g, 3.3 mmol) and methyl 4-amino-benzoate (0.5 g, 3.3 mmol) was cooled in an ice-bath, treated dropwise with a solution of potassium tert-butoxide (0.5 g, 4.9 mmol) in DMSO, stirred at room temperature overnight, quenched with water at 0° C. and extracted with ethyl acetate. The extracts were combined, washed sequentially with water and brine, dried over Na2SO4 and concentrated under vacuum to afford the title compound in 56% yield, identified by NMR and mass spectral analyses. 1H NMR (400 MHz, DMSO-d6): 9.5 (s, 1H), 8.22 (d, J=8 Hz, 1H), 8.06 (d, J=8.4 Hz, 2H), 7.46 (d, J=4 Hz, 2H), 7.30 (d, J=8.4 Hz, 2H), 6.91 (m, 1H), 3.92 (s, 3H). LCMS (ESI+) 272 (MH+).

Workup

  1. temperaturewas cooled in an ice-bath
  2. customquenched with water at 0° C.
  3. extractionextracted with ethyl acetate
  4. washwashed sequentially with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d5855f4a19ad44a0bf9390ea229c9e9a
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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