Anthranilic Acid → (2-Aminophenyl)(pyrrolidin-1-yl)methanone

HRID 1487224Notes

Reaction equation

HRID 1487224 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1>O1CCCC1>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:6]

Participants

4

Reactant 2

HCID 227Anthranilic AcidHCID 31268Pyrrolidine

Product 1

HCID 713136(2-Aminophenyl)(pyrrolidin-1-yl)methanoneYield 70.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-aminobenzoic acid (5.0 g, 36.5 mol) in tetrahydrofuran (50 mL) was added N,N′-carbonyldiimidazole (6.5 g, 40.1 mol) at 25° C., the resulting mixture was stirred for 1 hour at this temperature. Then pyrrolidine (3.5 g, 40.1 mmol) was added and the mixture was stirred overnight. The solvent was removed under the reduced pressure and the residue was washed with water and extracted with dichloromethane, the organic phase was dried over anhydrous sodium sulfate, concentrated to afford the product (2-aminophenyl)(pyrrolidin-1-yl)methanone (5.4 g, yield 66%), which was used for the next step without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 7.12-7.21 (m, 2H), 6.66-6.71 (m, 2H), 4.62 (br s, 2H), 3.63 (br s, 2H), 3.47 (br s, 2H), 1.87-1.94 (m, 4H).

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe solvent was removed under the reduced pressure
  3. washthe residue was washed with water
  4. extractionextracted with dichloromethane
  5. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a218da4ad05a48c6b17d76e69a493489
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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