1H-Indole-3-propanoic acid → HCID 57475146, compound

HRID 1095525Notes

Reaction equation

HRID 1095525 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12](O)=O)=[CH:2]1.[CH3:15][NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH2:23]>C(Cl)(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]2[N:16]([CH3:15])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:23]=2)=[CH:2]1

Participants

4

Reactant 2

HCID 37441H-Indole-3-propanoic acidHCID 78498N-Methyl-o-phenylenediamine

Product 1

HCID 57475146HCID 57475146, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3-indolepropionic acid (2.85 g, 15 mmol) and N-methyl-1,2-phenylenediamine (611 mg, 5.0 mmol) was stirred at 130° C. for 5H, during which a dark brown viscous mass forms, which was dissolved in chloroform (100 ml). The organic solution was then washed with 10% strength Na2CO3 solution (2×30 ml) and water, dried over Na2SO4 and concentrated i. vac. and the residue was purified by flash chromatography with cyclohexane/EA (1:1). Yield: 863 mg (Ind-54, 63%), colourless solid

Workup

  1. washThe organic solution was then washed with 10% strength Na2CO3 solution (2×30 ml) and water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated i
  4. customand the residue was purified by flash chromatography with cyclohexane/EA (1:1)

Sources & evidence

ORD record
ord-b776e3ba414d493e8cb0da143e47479c
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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