Hydrochloric Acid → 3-iodo-1H-indole-5-carboxylic acid

HRID 634191Notes

Reaction equation

HRID 634191 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[I:13]I.[OH-].[K+].S(=O)(O)[O-].[Na+].Cl>CN(C=O)C.O>[I:13][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:10]([OH:12])=[O:11])[CH:5]=2)[NH:1][CH:2]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 14797Potassium HydroxideHCID 742801H-Indole-5-Carboxylic AcidHCID 23665763Sodium Bisulfite

Product 1

HCID 509905183-iodo-1H-indole-5-carboxylic acidYield 192.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-indole-5-carboxylic acid (2.08 g, 12.89 mmol, Acros) in DMF (20 mL) was added I2 (3.27 g, 12.89 mmol) and KOH (1.807 g, 32.2 mmol). The reaction was stirred at RT for 1 h then the mixture was poured into ice and H2O (120 mL) containing sodium bisulfite (1.341 g, 12.89 mmol). The mixture was treated with 5 M HCl to pH=4. The resulting yellow solid was collected by filtration, washed with water and dried to give crude 3-iodo-1H-indole-5-carboxylic acid (7.13 g) as a yellow amorphous solid. MS (ESI, pos. ion) m/z: 288.0 (M+1). 1H NMR (400 MHz, MeOH) δ ppm 8.09-8.14 (1H, m), 7.88 (1H, dd, J=8.6, 1.6 Hz), 7.48 (1H, s), 7.45 (1H, d, J=8.6 Hz).

Workup

  1. filtrationThe resulting yellow solid was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-713205574d5b47de9bb25dfd0ba47727
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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