Acetic Acid → 3-Iodo-5-morpholinoaniline

HRID 1052486Notes

Reaction equation

HRID 1052486 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.C(O)(=O)C>C(O)C.O.C(=O)([O-])[O-].[Na+].[Na+].[Fe]>[I:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:3]=1)[NH2:8]

Participants

7

Reactant 2

HCID 176Acetic AcidHCID 584563064-(3-Iodo-5-nitrophenyl)morpholine

Product 1

HCID 901027553-Iodo-5-morpholinoanilineYield 81%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

4-(3-Iodo-5-nitrophenyl)morpholine (200 mg, 0.60 mmol, prepared according to WO 2008104754 A1 20080904) and powdered iron (142 mg, 2.54 mmol) were suspended in ethanol (2 ml) and acetic acid (240 μl, 4.20 mmol) and heated 3 h to 95° C. The reaction mixture was diluted with water, neutralised to pH=6 with sodium carbonate and extracted with ethyl acetate (×3). The organic phase was washed successively with water and brine, dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure. 179 mg (81% yield, 82% purity) of the title compound were obtained and used in the next synthetic step without further purification.

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. washThe organic phase was washed successively with water and brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-2e345514c1d14470ac73837d4a43139f
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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