Acetic Acid → 6-nitro-1H-indole-3-carbaldehyde

HRID 1749748Notes

Reaction equation

HRID 1749748 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13](O)(=[O:15])C.C1N2CN3CN(C2)CN1C3>O>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH:13]=[O:15])=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 785026-Nitro-1H-indole

Product 1

HCID 52100766-nitro-1H-indole-3-carbaldehydeYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

6-Nitroindole (1.0 g, 6.2 mmol) was successively added with acetic acid (2.5 mL), water (5.0 mL), and hexamethylenetetramine (1.2 g, 8.4 mmol), and then the mixture was stirred overnight at 120° C. in a sealed tube. The reaction mixture was added with water, and the precipitated solid was collected by filtration, and then dried to obtain 6-nitro-1H-indole-3-carboxaldehyde (0.91 g, 77%).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-716b45a55ff14e2fafb06dc475b3bfe6
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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