Aniline → HCID 564817, compound

HRID 1373079Notes

Reaction equation

HRID 1373079 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:16](=[O:22])[CH2:17][C:18]([O:20][CH3:21])=[O:19]>C(Cl)Cl>[CH3:21][O:20][C:18](=[O:19])[CH2:17][C:16]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:22]

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 123460Methyl malonyl chloride

Product 1

HCID 564817HCID 564817, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the ice-cooled solution of aniline (3,72 g, 40 mmol) in methylene chloride (300 mL) containing triethylamine (11.2 mL, 80 mmol) was added dropwise methyl 3-chloro-3-oxopropionate (5.37 mL, 50 mmol). The reaction mixture was then stirred at room temperature for 2 hours and washed with saturated aqueous NaHCO3 (2×150 mL). The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash chromatography over silica gel (ethyl acetate-hexane, 1:2) to give the title compound (7.2 g, 93.3%). 1H NMR (400 MHz, CDCl3) δ: 9.17 (brs, 1H), 7.53 (d, 2H), 7.32 (t, 2H), 7.10 (t, 1H), 3.80 (s, 2H).

Workup

  1. washwashed with saturated aqueous NaHCO3 (2×150 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography over silica gel (ethyl acetate-hexane, 1:2)

Sources & evidence

ORD record
ord-347e2020efbe4acb9c4302f1b0b6ea0b
Source dataset
uspto-grants-2007_01
Patent number
US07160902B2

Reaction notes

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