Ethyl 4-[isobutyl(propyl)amino]-3-nitrobenzoate → Ethyl 3-amino-4-[isobutyl(propyl)amino]benzoate

HRID 219821Notes

Reaction equation

HRID 219821 reaction equation
[CH2:1]([N:5]([CH2:20][CH2:21][CH3:22])[C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][C:7]=1[N+:17]([O-])=O)[CH:2]([CH3:4])[CH3:3].[H][H]>CCOC(C)=O.[Pd]>[NH2:17][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][C:6]=1[N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:20][CH2:21][CH3:22])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 67529011Ethyl 4-[isobutyl(propyl)amino]-3-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 67528421Ethyl 3-amino-4-[isobutyl(propyl)amino]benzoateYield 92.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 4-[isobutyl(propyl)amino]-3-nitrobenzoate (6 g, 0.0194 mol) in EtOAc (100 mL) was added Pd/C (600 mg). The reaction mixture was hydrogenated with hydrogen gas under 5 kg pressure for 3 h. The reaction mixture was filtered off Pd/C and filtrate was concentrated under reduced pressure to afford the title compound as yellow oil (5 g, 92%). 1H NMR (DMSO-d6, 400 MHz) δ 7.29 (s, 1H), 7.16 (d, 1H), 7.01 (d, 1H), 4.93 (s, 2H), 4.23 (q, 2H), 2.80 (t, 2H), 2.71 (t, 3H), 1.65 (m, 1H) 1.40 (m, 2H), 1.28 (t, 3H), 0.82 (m, 9H). LC/MS (Method A): 279.0 (M+H)+. HPLC (Method B) Rt 3.94 min (purity: 97.9%).

Workup

  1. filtrationThe reaction mixture was filtered off Pd/C and filtrate
  2. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-e14e82e0959640d59b8f766da4b2820c
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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