2-Nitro-5-(2-pyrrolidin-1-yl-ethyl)-benzoic acid methyl ester → 2-Amino-5-(2-pyrrolidin-1-yl-ethyl)-benzoic acid methyl ester

HRID 591840Notes

Reaction equation

HRID 591840 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:7]=[CH:6][C:5]=1[N+:17]([O-])=O>C1COCC1.[Pd]>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:7]=[CH:6][C:5]=1[NH2:17]

Participants

4

Reactant 1

HCID 666710792-Nitro-5-(2-pyrrolidin-1-yl-ethyl)-benzoic acid methyl ester

Product 1

HCID 666709102-Amino-5-(2-pyrrolidin-1-yl-ethyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-nitro-5-(2-pyrrolidin-1-yl-ethyl)-benzoic acid methyl ester in THF (16 mL) was added 10% palladium on charcoal (0.23 g). The resulting reaction mixture was hydrogenated under 40 psi for 2 hours, then the catalyst was filtered off and the filtrate concentrated under high vacuum to give 2-amino-5-(2-pyrrolidin-1-yl-ethyl)-benzoic acid methyl ester as a yellow oil. Yield: 1.04 g (89.6%). The crude material was used in the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. filtrationthe catalyst was filtered off
  3. concentrationthe filtrate concentrated under high vacuum

Sources & evidence

ORD record
ord-61a8722e735f4d6a95c03e67053ca12d
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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