Cesium carbonate → Methyl 3-((2-hydroxy-2-methylpropyl)amino)-4-nitrobenzoate

HRID 592326Notes

Reaction equation

HRID 592326 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:21][CH2:22][C:23]([CH3:26])([OH:25])[CH3:24].C(=O)(O)[O-].[Na+]>CS(C)=O.CCOC(C)=O>[OH:25][C:23]([CH3:26])([CH3:24])[CH2:22][NH:21][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 951022-Propanol, 1-amino-2-methyl-HCID 516892Sodium BicarbonateHCID 592761Methyl 3-fluoro-4-nitrobenzoate

Product 1

HCID 66690227Methyl 3-((2-hydroxy-2-methylpropyl)amino)-4-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-fluoro-4-nitrobenzoate (2.0 g, 10.04 mmol) in DMSO (10.04 mL) was added cesium carbonate (9.82 g, 30.1 mmol) and 1-amino-2-methylpropan-2-ol (0.985 g, 11.05 mmol). The reaction mixture was stirred at ambient temperature for 30 min. Saturated sodium bicarbonate and EtOAc were added to the mixture. The aqueous layer was extracted EtOAc (3×). The combined organics were washed with brine, dried over magnesium sulfate, filtered and concentrated to give the title compound without further purification (3.18 g): LC-MS [M+1]=269.2.

Workup

  1. extractionThe aqueous layer was extracted EtOAc (3×)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d9b5bc4cb38c4413901d1731512f56f2
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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