(2-Methylpropyl)(propyl)amine → Ethyl 4-[isobutyl(propyl)amino]-3-nitrobenzoate

HRID 219820

Reaction equation

HRID 219820 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH2:16]([NH:20][CH2:21][CH2:22][CH3:23])[CH:17]([CH3:19])[CH3:18]>C(O)C>[CH2:16]([N:20]([CH2:21][CH2:22][CH3:23])[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14])[CH:17]([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 520943(2-Methylpropyl)(propyl)amineHCID 21277355Ethyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 67529011Ethyl 4-[isobutyl(propyl)amino]-3-nitrobenzoateYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 4-fluoro-3-nitrobenzoate (7.4 g, 0.035 mol) in ethanol (100 mL) was added N-isobutyl-N-propylamine (11.98 g, 0.104 mol) at RT. The reaction mixture was heated at 60° C. for 12 h. It was then concentrated under reduced pressure. The residue was dissolved in water (40 mL) and was acidified to pH=4 with 1 M HCl solution. It was extracted with EtOAc (2×75 mL). The combined organic phases were washed with brine, dried over sodium sulphate and evaporated to afford the title compound (10 g, 93%) as a yellow oil. 1H NMR (DMSO-d6, 400 MHz) δ 8.20 (s, 1H), 7.92 (m, 1H), 7.38 (m, 1H), 4.28 (m, 2H), 3.15 (m, 2H), 3.03 (m, 2H), 1.86 (m, 1H), 1.51 (m, 2H) 1.28 (m, 3H), 0.78 (m, 9H). LC/MS (Method A): 309.0 (M+H)+. HPLC (Method B) Rt 5.05 min (purity: 99.4%).

Workup

  1. concentrationIt was then concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water (40 mL)
  3. extractionIt was extracted with EtOAc (2×75 mL)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-871ee87526334d34bbcd4d45c6b6b48e
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Linked notes

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