3-Nitrobenzoic acid → Tert-butyl 3-nitrobenzoate

HRID 2289802Notes

Reaction equation

HRID 2289802 reaction equation
NC1[CH:3]=[C:4]([CH:12]=CC=1)[C:5](OC(C)(C)C)=O.[N+:15]([C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21]([OH:23])=[O:22])([O-:17])=[O:16].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C([O-])([O-])=O.[Na+].[Na+]>CN(C1C=CN=CC=1)C.C1COCC1>[N+:15]([C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21]([O:23][C:4]([CH3:12])([CH3:5])[CH3:3])=[O:22])([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 84973-Nitrobenzoic acidHCID 10340Sodium CarbonateHCID 90495Di-tert-butyl dicarbonateHCID 2737408tert-Butyl-3-aminobenzoate

Product 1

HCID 11961369Tert-butyl 3-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

t-Butyl 3-aminobenzoate ##STR105## A mixture of 3-nitrobenzoic acid (5 g, 30 mmol), di-tert-butyl dicarbonate (20 g, 92 mmol), and DMAP (0.84 g, 6.9 mmol) in THF (60 mL) was stirred at 23° C. for 2 d. The mixture was poured onto ice-water, basified with Na2CO3 and extracted with CH2Cl2 (×3). The combined organic extracts were washed with brine, the solvents evaporated in vacuo and the residue was purified by column chromatography upon silica gel using hexanes-EtOAc (95:5) as eluant to give t-butyl 3-nitrobenzoate (5.4 g, 24 mmol) as a colourless oil.

Workup

  1. additionThe mixture was poured onto ice-water
  2. extractionextracted with CH2Cl2 (×3)
  3. washThe combined organic extracts were washed with brine
  4. customthe solvents evaporated in vacuo
  5. customthe residue was purified by column chromatography upon silica gel

Sources & evidence

ORD record
ord-a82c7cac7b25457fa704eff5e7c71463
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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