Citric Acid → 1-Methyl-6-nitro-1H-indole-3-carbonitrile

HRID 1517960Notes

Reaction equation

HRID 1517960 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]#[N:14])=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[K].[CH3:16]C(C)([O-])C.CI.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.O>[CH3:16][N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[C:8]([C:13]#[N:14])=[CH:9]1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 6328Methyl iodideHCID 2831796-Nitro-1H-indole-3-carbonitrileHCID 50987170Potassium tertbutoxide

Product 1

HCID 593349091-Methyl-6-nitro-1H-indole-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.6 g 6-nitro-1H-indole-3-carbonitrile are dissolved in 45 ml of tetrahydrofuran, combined with 1 g potassium-tert.-butoxide and stirred for 30 minutes. Then a solution of 560 μl methyl iodide in 5 ml of tetrahydrofuran is slowly added dropwise and the mixture is stirred for 5 hours. The solvents are eliminated in vacuo, water is added and the pH is adjusted to 4 by the addition of citric acid. The solid is suction filtered and washed with water and some cold methanol.

Workup

  1. stirringthe mixture is stirred for 5 hours
  2. additionis added
  3. filtrationfiltered
  4. washwashed with water

Sources & evidence

ORD record
ord-e158ca5e18fb4af4baf0dcfad4d2759d
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

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